Dimethylformamide → 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

HRID 877142Notes

Reaction equation

HRID 877142 reaction equation
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@@H:13]2[C:18]([OH:20])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1[CH:34]=[CH:35][C:36]2N(O)[N:40]=[N:39][C:37]=2C=1.[C:43]([O:47][C:48]([N:50]([C:52]([C@@H]1CCNC1)=O)N)=[O:49])([CH3:46])([CH3:45])[CH3:44].CN(C)C=[O:62]>>[C:43]([O:47][C:48]([N:50]1[CH2:34][CH2:35][C@@H:36]([C:37]([NH:39][NH:40][C:18]([C@H:13]2[CH2:12][CH2:11][C@@H:10]3[CH2:17][N:14]2[C:15](=[O:16])[N:9]3[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:20])=[O:62])[CH2:52]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68761009HCID 68761009, compoundHCID 71283510HCID 71283510, compound

Product 1

HCID 86719961trans-3-[N'-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl esterYield 43%

Procedure

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.

Sources & evidence

ORD record
ord-11314402243543d1a28f9d1b161c88ba
Source dataset
uspto-grants-2015_03
Patent number
US08987297B2

Reaction notes

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