(S)-ethyl 3-(3-aminophenyl)-3-(benzyloxycarbonylamino)propanoate → (R)-ethyl 3-(3-aminophenyl)-3-(benzyloxycarbonylamino)propanoate

HRID 735612Notes

Reaction equation

HRID 735612 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(OC(N[C@@H](C1C=CC=C([N+]([O-])=O)C=1)CC(OCC)=O)=O)C1C=CC=CC=1>[Fe]>[NH2:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57842670(S)-ethyl 3-(3-aminophenyl)-3-(benzyloxycarbonylamino)propanoateHCID 57842698(R)-ethyl 3-(benzyloxycarbonylamino)-3-(3-nitrophenyl)propanoate

Product 1

HCID 57842606(R)-ethyl 3-(3-aminophenyl)-3-(benzyloxycarbonylamino)propanoateYield 95%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Using a procedure analogous to that used to prepare 34C, 39B (3.1 g, 8.3 mmol) was reacted with Fe to afford 39C (2.7 g, 95%) as a white solid. MS (ESI) m/z 343.35 (M+H)+.

Sources & evidence

ORD record
ord-999226400dfc4bd1868c130ad6bb47c8
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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