Norfenefrine → (2S,4EZ)-N-[(2RS)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-4-(methoxy-imino)-1-[(3',4'-dichloro[1,1'-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxamide

HRID 1349314Notes

Reaction equation

HRID 1349314 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:41]=[C:42]([OH:46])[CH:43]=[CH:44][CH:45]=1)[OH:39]>>[OH:39][CH:38]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([OH:46])[CH:41]=1)[CH2:37][NH:36][C:16]([C@@H:9]1[CH2:10][C:11](=[N:13][O:14][CH3:15])[CH2:12][N:8]1[C:6]([C:30]1[CH:29]=[CH:28][C:27]([C:22]2[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=2)=[CH:32][CH:31]=1)=[O:7])=[O:18]

Participants

4

Reactant 3

HCID 4538NorfenefrineHCID 27581564-(3,4-Dichlorophenyl)benzoic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725645(2S,4EZ)-N-[(2RS)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-4-(methoxy-imino)-1-[(3',4'-dichloro[1,1'-biphenyl]-4-yl)carbonyl]-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 3-[(1RS)-2-amino-1-hydroxyethyl]phenol, the title compound was obtained in 91% purity by HPLC. MS(ESI+): m/z=543.

Sources & evidence

ORD record
ord-38ee416d3619455588beb7b387d87f92
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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