4-Boc-1-piperazineacetic acid

4-Boc-1-piperazineacetic acid - Names and Identifiers

Name	4-Boc-1-piperazineacetic acid
Synonyms	BOC-4-CARBOXYMETHYLPIPERAZINE 4-Boc-1-piperazineacetic acid 1-BOC-4-CARBOXYMETHYL PIPERAZINE 2-(1-BOC-PIPERAZIN-4-YL)-ACETIC ACID 2 H2O 2-(1-Boc-piperazin-4-yl)-acetic acid dihydrate 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)acetic acid [4-(tert-butoxycarbonyl)piperazin-1-yl]aceticacid2H2O 4-[(1,1-DIMETHYLETHOXY)CARBONYL]-1-PIPERAZINEACETIC ACID 2-(1-TERT-BUTOXYCARBONYL-PIPERAZIN-4-YL)-ACETIC ACID 2 H2O [4-(tert-butoxycarbonyl)piperazin-1-yl]acetic acid dihydrate 2-(1-TERT-BUTOXYCARBONYL-PIPERAZIN-4-YL)-ACETIC ACID 2-HYDRATE
CAS	156478-71-6
InChI	InChI=1/C11H20N2O4/c1-11(2,3)17-10(16)13-6-4-12(5-7-13)8-9(14)15/h4-8H2,1-3H3,(H,14,15)

4-Boc-1-piperazineacetic acid - Physico-chemical Properties

Molecular Formula	C11H20N2O4
Molar Mass	244.29
Density	1.174
Boling Point	365.5±37.0 °C(Predicted)
Flash Point	174.851°C
Vapor Presure	0mmHg at 25°C
pKa	2.40±0.10(Predicted)
Storage Condition	Keep in dark place,Sealed in dry,Room Temperature
Refractive Index	1.501
MDL	MFCD02682402

4-Boc-1-piperazineacetic acid - Risk and Safety

Hazard Symbols	Xi - Irritant
WGK Germany	3
Hazard Class	IRRITANT

4-Boc-1-piperazineacetic acid - Reference Information

Uses

4-Boc-1-piperazine acetic acid is an organic intermediate.

Preparation

4-Boc-1-piperazine acetic acid can be prepared from piperazine-1-carboxylic acid tert-butyl ester as raw material. 4-(2-ethoxy-2-oxoethyl) piperazin-1-carboxylic acid tert-butyl ester, and then hydrolyze the ester group to obtain 4-Boc-1-piperazinacetic acid. Potassium carbonate (3.71g,26.8mmol) and ethyl bromoacetate (1.2mL,10.8mmol) were added to DMF(14mL) solution of stirred piperazine-1-carboxylate (2g,10.7mmol) under room temperature and inert atmosphere. The reaction mixture was stirred at room temperature for 16h. After consumption of the feedstock (monitored by TLC), the reaction mixture was diluted with water (50mL) and extracted with EtOAc(2 × 50mL). The combined organic extract was dried with anhydrous Na2SO4 and concentrated under reduced pressure to obtain 4-(2-ethoxy-2-oxoethyl) piperazine-1-carboxylic acid tert-butyl ester (2.8g,10.29mmol,95%) as a yellow oil. 1H NMR(500MHz,DMSO-d6):δ4.12-4.00(m,2H),3.30(s,4H),3.23(s,2H),2.45(t,J = 4.6Hz,4H),1.39(s,9H),1.18(t,J = 7.1Hz,3H)4-Boc-1-piperazine acetic acid at 0 ℃, lithium hydroxide (1.29g,30.8mmol) was added to a solution of a mixture of stirred 4-(2-ethoxy-2-oxoethyl) piperazine-1-carboxylic acid tert-butyl ester (2.8g,10.29mmol) of THF ∶ MeOH ∶ water (3:1 ∶ 1,30mL). The reaction mixture was gradually warmed to room temperature and stirred for 3h. After consumption of the feedstock (monitored by TLC), the volatiles were concentrated under reduced pressure. The residue was then acidified to pH 4 to pH 5 with a 5% citric acid solution and extracted with EtOAc(2 × 100mL). The combined organic extract was dried with anhydrous Na2SO4 and concentrated under reduced pressure to obtain 4-Boc-1-piperazine acetic acid (200mg, crude) as a yellow oil, which can be used in the next step without further purification. LC-MS: m/z 245.1[M-H] (purity 71.81%) at 1.06RT.

Last Update：2024-04-09 20:52:54