4-(4-Chlorophenoxy)aniline → (S)-2-amino-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)propanamide

HRID 1630054Notes

Reaction equation

HRID 1630054 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:16]([O:23][CH2:24][C@H:25]([NH:29]C(OC(C)(C)C)=O)[C:26](O)=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[NH2:29][C@@H:25]([CH2:24][O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:26]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)=[O:27]

Participants

3

Reactant 2

HCID 75784-(4-Chlorophenoxy)anilineHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 67009405(S)-2-amino-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)propanamideYield 48.7%

Procedure

Proceeding as in Reference 5, but substituting 4-(4-chlorophenoxy)aniline (329 mg, 1.5 mmoles) and (S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid (487 mg, 1.65 mmoles), gave (S)-2-amino-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)propanamide (290 mg, 48%).

Sources & evidence

ORD record
ord-2ecab0924eef4d368fddbdf870c86058
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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