FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
Na-Fmoc-Ng-2,2,4,6,7-pentamethyl-dihydrobenzofuran-5-sulfonyl-L-arginine
CAS: 154445-77-9;15445-77-9
Molecular Formula: C34H40N4O7S
FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE - Names and Identifiers
FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE - Physico-chemical Properties
| Molecular Formula | C34H40N4O7S |
| Molar Mass | 648.77 |
| Density | 1.37±0.1 g/cm3(Predicted) |
| Melting Point | 132°C |
| Specific Rotation(α) | -5.5 º (c=1,DMF) |
| Solubility | DMF (Sparingly), DMSO (Slightly), Methanol (Slightly) |
| Appearance | Solid |
| Color | White to Off-White |
| BRN | 8302671 |
| pKa | 3.83±0.21(Predicted) |
| Storage Condition | Store at -15°C to -25°C. |
| Refractive Index | 1.648 |
| MDL | MFCD00235804 |
FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 1 |
| HS Code | 2935 90 90 |
| Hazard Class | IRRITANT |
FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE - Reference Information
| introduction | arginine is an essential amino acid that can be naturally produced in the body. In life science research, in order to avoid the generation of by-products, the amino and guanidine groups of arginine must be protected. Fmoc-Pbf-arginine uses Fmoc (9-fluorenomethoxycarbonyl) to protect the amino group, and Pbf(2,2,4,6, 7-pentamethylbenzofuran-5-sulfonyl) to protect the guanidine group. Amino acid derivatives. |
| preparation | (1) esterification a1. Add 100L of anhydrous ethanol into a pre-dried 300L reaction kettle, cool the temperature to -5 ~-10 ℃ through ice brine, and add 13L of dichlorosulfoxide dropwise. B1. Add Arg.HCl21.5kg of D type, turn off the ice brine, and naturally raise the temperature to room temperature for 24 hours. c1. The reaction was heated to 35 ℃, TLC point plate followed the reaction, and the reaction ended about 48h. D1. Concentration: After the reaction is over, the Arg · Oet · 2HCl intermediate of the oil is obtained by concentration under reduced pressure. (2) introduction of Boc group a2. Add 150L of water into a 300L reactor, then add 25.2kg of sodium bicarbonate, and stir; Gradually add Arg · Oet · 2HCl oil; Add 30L of tetrahydrofuran; Add (Boc)2O in batches, stir 26.2kg, and react at room temperature; TLC method point plate tracks the reaction and starts processing when Arg · Oet · 2HCl reaction is finished. b2. Acidification: adjust the pH3-4 after the reaction is completed and extract with petroleum ether/ethyl acetate (50L:25L); c2. Add salt to saturate, call back the PH6-7, extract the product with ethyl acetate, and wash the organic phase with saturated salt water. D2. Drying: Add 60kg of anhydrous sodium sulfate to the organic phase (ethyl acetate solution with product) and dry for 8 hours. E2. Purification and concentration: filter out the sodium sulfate solid and distill the ethyl acetate phase under reduced pressure. The Boc-ArgOet.HCl oil obtained after concentration. (3) Introduction of Pbfa3. Add the Boc-ArgOet.HCl obtained in step 2, Pbf-Cl31.9kg, acetone 200L, potassium carbonate 41.7kg, stir, add a small amount of water, maintain the temperature of 40-45 ℃, monitor the reaction with TLC, perform suction filtration after Boc-ArgOet.HCl complete reaction, b3. Filter by suction, remove solid insoluble matter, distill acetone under reduced pressure, and concentrate to obtain Boc-Arg(Pbf)Oet oil for later use. (4) Take off Boca4. In a dried 300L reactor, 120L of 3NHCl/ethyl acetate solution was added, Boc-Arg(Pbf)Oet oil was added under stirring, and the temperature was maintained at 10-15 ℃ and stirred at room temperature. B4. After boc removal is completed, add water to wash, wash the product to the water phase, and add appropriate amount of sodium carbonate to adjust the water phase pH7. (5) saponification a5. The water obtained in step (4) is added to 95% 100L of ethanol, stirred, and 10NNaOH aqueous solution is added dropwise to adjust the pH11-12 for saponification. b5. After the saponification reaction is completed, adjust the pH value of the reaction solution with 6NHCl to 7, and cool the temperature to -10-0 ℃ to freeze and crystallize; centrifuge, the solid is stirred and washed once with ethyl acetate, and centrifuged to collect the solid; recrystallize to obtain H-Arg(Pbf)OH solid. (6)Fmoc-Pbf-arginine synthesis a6. H-Arg(Pbf)-OH, water 120L and THF were added to the reaction kettle, and the PH = 8.5 was adjusted by Na2CO3. B6. Gradually add Fmoc-Osu (fluorene methoxycarbonyl succinimide), control the temperature 15-20 ℃,PH = 8-9 to finish the reaction of Arg(Pbf), and try to avoid excessive Fmoc-Osu. TLC point plate tracks the reaction, starting from the addition of the Fmoc-Osu, the reaction time is 6 hours. C6. Purification: Extraction with petroleum ether/ethyl acetate (2:1); The aqueous phase was acidified with HCl to pH = 3 and stirred for 2 hours. Acidification temperature 0-10 ℃; Add ethyl acetate to extract the product; Wash with saturated salt water until pH 6; Dry anhydrous sodium sulfate, vacuum filter to remove solids, concentrate filtrate, concentrate under reduced pressure to obtain solids, and vacuum dry to obtain products. The purity of the product is 99.6%, the maximum mono-hybrid 0.09%, and the L-type isomer is 0.15%. |
Last Update：2024-04-09 20:49:11
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