반응 #155539

ord-df9fb21b04d84e34ab992cdc803aa414

반응 방정식

CC(C)(C)OC(=O)N(N)C(=O)[C@@H]1CCNC1
(R)—N-tert-butoxycarbonyl-pyrrolidin-3-carboxylic acid hydrazide
O=C(O)[C@H]1CC[C@@H]2CN1C(=O)N2OCc1ccccc1
trans-6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid
CCN=C=NCCCN(C)C.Cl
EDC hydrochloride
CN(C)C=O
N,N-dimethyl formamide
On1nnc2ccccc21
HOBt
→
CC(C)(C)OC(=O)N1CC[C@@H](C(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3OCc2ccccc2)C1
title compound
수율 43.0%
CC(C)(C)OC(=O)N1CC[C@@H](C(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3OCc2ccccc2)C1
trans-3-[N′-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester
수율 43.0%

반응물

CC(C)(C)OC(=O)N(N)C(=O)[C@@H]1CCNC1
(R)—N-tert-butoxycarbonyl-pyrrolidin-3-carboxylic acid hydrazide
O=C(O)[C@H]1CC[C@@H]2CN1C(=O)N2OCc1ccccc1
trans-6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid
CCN=C=NCCCN(C)C.Cl
EDC hydrochloride
CN(C)C=O
N,N-dimethyl formamide
On1nnc2ccccc21
HOBt

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

By using the procedure described in Step-1 of Example-1, and by using trans-6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (15.7 gm, 0.057 mol), N,N-dimethyl formamide (390 ml), EDC hydrochloride (16.24 gm, 0.085 mol), HOBt (11.48 gm, 0.085 mol), (R)—N-tert-butoxycarbonyl-pyrrolidin-3-carboxylic acid hydrazide (13.7 gm, 0.06 mol) to provide the title compound in 11.94 gm quantity, 43% yield as a white solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08822450B2uspto-grants-2014_09