BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID

Base Information

• Chemical Name: BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID
• CAS No.: 54256-41-6
• Molecular Formula: C10H17NO4
• Molecular Weight: 215.249
• Hs Code.: 2924299090
• Mol file: 54256-41-6.mol

Synonyms:TERT-BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID;BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID;Boc-DL-cyclopropylglycine

Chemical Property of BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID

Chemical Property:

• PSA: 75.63000
• LogP: 1.76680
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99% ^*data from raw suppliers

Boc-DL-cyclopropylglycine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID

There total 9 articles about BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.6%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-amino-2-cyclopropylacetic acid (49607-01-4) → N-(R)-2-(tertbutoxycarbonylamino)-2-cyclopropylacetic acid (54256-41-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 0.5h;

Reference yield:

tert-butyl (S)-(1-cyclopropyl-2-oxoethyl)carbamate → N-(R)-2-(tertbutoxycarbonylamino)-2-cyclopropylacetic acid (54256-41-6) + (2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid (155976-13-9)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; tert-butyl alcohol; at 20 ℃; for 1h; Overall yield = 17 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.202005599

Reference yield:

(S)-tert-butyl (1-cyclopropylbuta-2,3-dien-1-yl)carbamate → N-(R)-2-(tertbutoxycarbonylamino)-2-cyclopropylacetic acid (54256-41-6) + (2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid (155976-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ozone; triphenylphosphine / dichloromethane / -78 °C / Inert atmosphere

2: sodium chlorite; sodium dihydrogenphosphate / tert-butyl alcohol; water / 1 h / 20 °C / Inert atmosphere

With sodium chlorite; sodium dihydrogenphosphate; ozone; triphenylphosphine; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1002/anie.202005599

upstream raw materials:

di-tert-butyl dicarbonate

(R)-2-amino-2-cyclopropylacetic acid

C₁₆H₂₇NO₄

C₁₁H₁₉NO₂

Downstream raw materials:

(R)-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-1-methyl-pyrrolidine-2-carbonyl]-amino}-cyclopropyl-acetic acid methyl ester

(R)-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-1-methyl-pyrrolidine-2-carbonyl]-amino}-cyclopropyl-acetic acid

Refernces

• 1、 Carreira, Erick M.,Glatz, Fabian,Petrone, David A.. "Ir-Catalyzed Enantioconvergent Synthesis of Diversely Protected Allenylic Amines Employing Ammonia Surrogates". . p. 16404 - 16408. Retrieved 2020/07/27.
• 2、 -. "SELECTIVE KINASE INHIBITORS". Paragraph 0531; 0532. . Retrieved 2013/06/06.