beta-Alaninamide → (2S,4EZ)-N-(3-amino-3-oxopropyl)-1-[(2',6'-dimethyl[1,1'-biphenyl]-4-yl)carbonyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1349320Notes

Reaction equation

HRID 1349320 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]=[C:22]([CH3:26])[C:21]=1[C:27]1[CH:32]=[CH:31][C:30](C(O)=O)=[CH:29][CH:28]=1.[NH2:36][CH2:37][CH2:38][C:39]([NH2:41])=[O:40]>>[NH2:41][C:39](=[O:40])[CH2:38][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:21]2[C:22]([CH3:26])=[CH:23][CH:24]=[CH:25][C:20]=2[CH3:19])=[CH:32][CH:31]=1)=[O:7])=[O:18]

Participants

4

Reactant 3

HCID 192802beta-AlaninamideHCID 219372914-(2,6-Dimethylphenyl)benzoic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725652(2S,4EZ)-N-(3-amino-3-oxopropyl)-1-[(2',6'-dimethyl[1,1'-biphenyl]-4-yl)carbonyl]-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′,6′-dimethyl[1,1′-biphenyl]-4-carboxylic acid, and 3-aminopropionamide, the title compound was obtained in 87% purity by HPLC. MS(ESI+): m/z=437.

Sources & evidence

ORD record
ord-576101db3246489dbda1d05d300867b2
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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