m-Tyramine → (2S,4EZ)-1-[(2',3-dimethyl[1,1'-biphenyl]-4-yl)carbonyl]-N-[2-(3-hydroxyphenyl)ethyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1745329Notes

Reaction equation

HRID 1745329 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.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][C:29](C(O)=O)=[C:28]([CH3:35])[CH:27]=1.[NH2:36][CH2:37][CH2:38][C:39]1[CH:40]=[C:41]([OH:45])[CH:42]=[CH:43][CH:44]=1>>[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][C:29]([C:6]([N:8]2[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]2[C:16]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([OH:45])[CH:40]=2)=[O:18])=[O:7])=[C:28]([CH3:35])[CH:27]=1

Participants

4

Reactant 3

HCID 11492m-TyramineHCID 219372462',3-Dimethyl[1,1'-biphenyl]-4-carboxylic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725657(2S,4EZ)-1-[(2',3-dimethyl[1,1'-biphenyl]-4-yl)carbonyl]-N-[2-(3-hydroxyphenyl)ethyl]-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, 2′,3-dimethyl[1,1-biphenyl]-4carboxylic acid, and 3-(2-aminoethyl)phenol, the title compound was obtained in 89% purity by HPLC. MS(ESI+): m/z=486.

Sources & evidence

ORD record
ord-3b574caaa601416ea13d427af02f18ea
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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