Phenylethanolamine → (2S,4EZ)-1-[(3',4'-dichioro[1,1'-biphenyl]-4-yl)carbonyl]-N-[(2RS)-2-hydroxy-2-phenylethyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1745313Notes

Reaction equation

HRID 1745313 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)=[O:7])(C)(C)C.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30](C(O)=O)=[CH:29][CH:28]=2)[CH:23]=[CH:24][C:25]=1[Cl:26].[NH2:36][CH2:37][CH:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[OH:39]>>[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH:28]=[CH:29][C:30]([C:6]([N:8]3[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]3[C:16]([NH:36][CH2:37][CH:38]([OH:39])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:18])=[O:7])=[CH:31][CH:32]=2)[CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

4

Reactant 3

HCID 1000PhenylethanolamineHCID 27581564-(3,4-Dichlorophenyl)benzoic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725642(2S,4EZ)-1-[(3',4'-dichioro[1,1'-biphenyl]-4-yl)carbonyl]-N-[(2RS)-2-hydroxy-2-phenylethyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 3′,4′-dichloro[1,1-biphenyl]-4-carboxylic acid, and (1RS)-2-amino-1-phenylethanol, the title compound was obtained in 89% purity by HPLC. MS(ESI+): m/z=527.

Sources & evidence

ORD record
ord-8e4e80b7e99c4cdbad16e0ccc16aa11f
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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