tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate
• CAS No.: 1621435-13-9
• Molecular Formula: C₂₉H₃₈N₂O₇
• Molecular Weight: 526.63
• Mol file: 1621435-13-9.mol

Synonyms:tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate

Chemical Property of tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate

There total 11 articles about tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate 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: 79.3%

(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate hydrochloride (67580-86-3) + 1-(tert-butoxycarbonyl)-2-(hydroxymethyl)pyrrolidine-2-carboxylic acid (1621435-12-8) → tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate (1621435-13-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

Reference yield: 52.0%

1-(tert-butoxycarbonyl)-2-(hydroxymethyl)pyrrolidine-2-carboxylic acid (1621435-12-8) + (2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate oxalate (42001-91-2) → tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate (1621435-13-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃; for 16h;

Reference yield:

2-((benzyloxy)methyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1194030-71-1) → tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate (1621435-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C

With palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

upstream raw materials:

N‐(tert‐butoxycarbonyl)‐O‐benzyl‐L‐threonine benzyl ester

(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate hydrochloride

1-(tert-butoxycarbonyl)-2-(hydroxymethyl)pyrrolidine-2-carboxylic acid

L-proline

Downstream raw materials:

(2S,3R)-3-hydroxy-2-(5-isobutyryl-1-oxo-2,5-diazaspiro[3.4]octan-2-yl)butanamide

benzyl (2S,3R)-2-(5-acetyl-1-oxo-2,5-diazaspiro[3.4]octan-2-yl)-3-(benzyloxy)butanoate

tert-butyl 2-((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl)-1-oxo-2, 5-diazaspiro [3.4] octane-5-carboxylate

tert-butyl (R)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro [3.4]octane-5-carboxylate