Benzyl succinimido carbonate → (R)-ethyl 3-(benzyloxycarbonylamino)-3-(3-nitrophenyl)propanoate

HRID 735611Notes

Reaction equation

HRID 735611 reaction equation
Cl.[NH2:2][C@@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:19]([O:26][C:27](ON1C(=O)CCC1=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([O:26][C:27]([NH:2][C@@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 86614936(r)-Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride salt

Product 1

HCID 57842698(R)-ethyl 3-(benzyloxycarbonylamino)-3-(3-nitrophenyl)propanoateYield 83%

Procedure

Using a procedure analogous to that used to prepare 34B, 39A (2.75 g, 10 mmol) was reacted with N-(Benzyloxycarbonyloxy)succinimide to afford 39B (3.1 g, 83%) as a white solid. MS (ESI) m/z 395.13 (M+Na)+.

Sources & evidence

ORD record
ord-864721526b044b439100aa49d96727d8
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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