1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid

Base Information

• Chemical Name: 1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid
• CAS No.: 1426324-05-1
• Molecular Formula: C₁₇H₁₈F₃NO₄
• Molecular Weight: 357.329

Synonyms:1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid

Chemical Property of 1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid

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Technology Process of 1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid

There total 1 articles about 1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic 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: 92.0%

(3a'R,4'S)-4'-(benzyloxy)tetrahydrodispiro[cyclopropane-1,2'-pyrrolo[1,2-b]isoxazole-3',1''-cyclopropane] (1426324-04-0) + trifluoroacetic acid (76-05-1) → 1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid (1426324-05-1)

Guidance literature:

In acetonitrile; for 0.25h; Microwave irradiation; Heating;

DOI:10.1007/s00726-012-1401-0

Reference yield: 83.0%

L-Valine methyl ester (4070-48-8) + 1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid (1426324-05-1) → methyl N-({1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropyl}carbonyl)-L-valinate (1426324-09-5)

Guidance literature:

1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.333333h;

L-Valine methyl ester; With triethylamine; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1007/s00726-012-1401-0

Reference yield: 27.0%

acetic acid tert-butyl ester (540-88-5) + 1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid (1426324-05-1) → C21H26F3NO4 (1426324-06-2)

Guidance literature:

With perchloric acid; at 20 ℃; for 20h;

DOI:10.1007/s00726-012-1401-0

upstream raw materials:

(3a'R,4'S)-4'-(benzyloxy)tetrahydrodispiro[cyclopropane-1,2'-pyrrolo[1,2-b]isoxazole-3',1''-cyclopropane]

trifluoroacetic acid

Downstream raw materials:

methyl N-({1-[(2R,3S)-3-(benzyloxy)-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropyl}carbonyl)-L-valinate

tert-butyl 1-((2R,3S)-3-(benzyloxy)-1-{N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl}pyrrolidin-2-yl)cyclopropanecarboxylate

methyl N-({1-[(2R,3S)-3-(benzyloxy)pyrrolidin-2-yl]cyclopropyl}carbonyl)-L-valinate

methyl N-[(1-{(2R,3S)-3-(benzyloxy)-1-[N-(tert-butoxycarbonyl)-L-phenylalanyl]pyrrolidin-2-yl}cyclopropyl)carbonyl]-L-valinate

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