(2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
CAS No.:296782-55-3
Molecular Formula:C₂₃H₂₇F₃N₂O₇
Molecular Weight:500.472
Hs Code.:

Synonyms:(2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

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Chemical Property of (2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

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Technology Process of (2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

There total 6 articles about (2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 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: 68.0%

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: 296782-15-5
(2S,5R)-5-Formyl-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

: 296782-55-3
(2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: With potassium tert-butylate; In dichloromethane; at -78 ℃; for 5h;
DOI:10.1002/1099-0690(200007)2000:14<2571::aid-ejoc2571>3.0.co;2-d

Reference yield:

: 183996-24-9
(2S,5S)-1-benzyl-5-hydroxymethylpyrrolidine-2-carboxylic acid tert-butyl ester

: 296782-55-3
(2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / TEA; DMAP / CH₂Cl₂ / 12 h

2: 94 percent / H₂ / 20percent Pd(OH)2 / methanol / 4 h

3: 89 percent / pyridine / CH₂Cl₂ / 1.5 h

4: 98 percent / TBAF / tetrahydrofuran / 2.5 h / -40 - 20 °C

5: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -60 - 20 °C

6: 68 percent / tBuOK / CH₂Cl₂ / 5 h / -78 °C

With pyridine; dmap; oxalyl dichloride; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; 20percent Pd(OH)2; In tetrahydrofuran; methanol; dichloromethane; 1: Substitution / 2: Hydrogenolysis / 3: Acylation / 4: Substitution / 5: Oxidation / 6: Horner-Emmons olefination;
DOI:10.1002/1099-0690(200007)2000:14<2571::aid-ejoc2571>3.0.co;2-d

Reference yield:

: 296782-34-8
1-benzyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

: 296782-55-3
(2S,5R)-5-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / H₂ / 20percent Pd(OH)2 / methanol / 4 h

2: 89 percent / pyridine / CH₂Cl₂ / 1.5 h

3: 98 percent / TBAF / tetrahydrofuran / 2.5 h / -40 - 20 °C

4: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -60 - 20 °C

5: 68 percent / tBuOK / CH₂Cl₂ / 5 h / -78 °C

With pyridine; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; 20percent Pd(OH)2; In tetrahydrofuran; methanol; dichloromethane; 1: Hydrogenolysis / 2: Acylation / 3: Substitution / 4: Oxidation / 5: Horner-Emmons olefination;
DOI:10.1002/1099-0690(200007)2000:14<2571::aid-ejoc2571>3.0.co;2-d