78879-20-6
N-BOC-L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
CAS: 78879-20-6
Molecular Formula: C15H19NO4
78879-20-6 - Names and Identifiers
| Name | N-BOC-L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid |
| Synonyms | Boc-Tic Boc-L-Tic Boc-Tic-OH Boc-Tic-Oh Boc-L-Tic-OH (Tert-Butoxy)Carbonyl Tic-OH Boc-L-Tetrahydroisoquinoline-3-COOH N-BOC-L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (S)-()-N-BOC-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID (S)-(+)-N-BOC-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID N-T-BUTOXYCARBONYL-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID |
| CAS | 78879-20-6 |
| InChI | InChI=1/C15H19NO4/c1-15(2,3)20-14(19)16-9-11-7-5-4-6-10(11)8-12(16)13(17)18/h4-7,12H,8-9H2,1-3H3,(H,17,18)/p-1/t12-/m0/s1 |
78879-20-6 - Physico-chemical Properties
| Molecular Formula | C15H19NO4 |
| Molar Mass | 277.32 |
| Density | 1.1311 (rough estimate) |
| Melting Point | 125-126.5 °C |
| Boling Point | 420.18°C (rough estimate) |
| Flash Point | 218.5°C |
| Solubility | soluble in Methanol |
| Vapor Presure | 1.97E-08mmHg at 25°C |
| Appearance | Solid |
| Color | White to off-white |
| BRN | 4297114 |
| pKa | 3.88±0.20(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.5080 (estimate) |
78879-20-6 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29334900 |
| Hazard Class | IRRITANT |
78879-20-6 - Reference Information
| description | N-BOC-L-1,2,3, 4-tetrahydroisoquinoline-3-carboxylic acid is an organic intermediate, (3S)-1,2,3, 4-tetrahydroisoquinoline-3-carboxylic acid can be obtained from L-phenylalanine as a starting material, and then the protective group is obtained as N-BOC-L-1,2,3, 4-tetrahydroisoquinoline-3-carboxylic acid. |
| preparation | preparation (3S)-1,2,3, 4-tetrahydroisoquinoline-3-carboxylic acid to 4.0g(24.2mmol) of L-phenylalanine was added dropwise 21.6ml of formaldehyde and then 36ml of 35% concentrated hydrochloric acid. The obtained suspension was heated to 95 ° C. And stirred for 2H, and phenylalanine was completely dissolved. After 2.5h of reaction, colorless precipitate began to form. L-phenylalanine disappeared, and 4.2g of a pale yellow solid was obtained by Suction filtration. The obtained pale yellow solid was added to 86ml of ethanol (80%) at 80 ° C. In an oil bath to dissolve a colorless solid, cooled to room temperature, and 2N NaOH solution was slowly added dropwise to precipitate a colorless precipitate, at maximum precipitation was filtered to give 4.17g(97.5%) of the title compound as a colorless solid. ESI-MS(m/e)176[M H]. Preparation of (3S)-N-Boc-1,2,3, 4-tetrahydroisoquinoline-3-carboxylic acid 2.5g(62.2mmol) of sodium hydroxide was dissolved in 62ml of water under ice bath, then 10g(56.5mmol) of (3S)-1,2,3, 4-tetrahydroisoquinoline-3-carboxylic acid was added to make a suspension. 14.8g(67.8mmol) of (Boc)2O dissolved in 40ml of tetrahydrofuran was added to the suspension. The reaction mixture was stirred for 24h. During the reaction, the CO2 generated by the reaction was continuously removed. When the solution became clear, TLC (methanol/Chloroform: 1:10) showed (3S)-1,2, the 3, 4-tetrahydroisoquinoline-3-carboxylic acid disappeared and the reaction was stopped. The reaction mixture was concentrated under reduced pressure to remove Tetrahydrofuran, and the resulting oil was dissolved in ethyl acetate. The resulting solution was washed sequentially with 5% KHSO4 and saturated aqueous NaCl. The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure. The resulting oil was dissolved in ether to dissolve the crystals and filtered to give 14.8g(95%) of the title compound as a colorless solid. ESI-MS(m/e)278[M H]. |
Last Update：2024-04-09 21:50:46
