(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → 1-(N'-(3,5-Difluorophenylacetyl)-L-alaninyl)amino 3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 1369689Notes

Reaction equation

HRID 1369689 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=O)[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:18][CH:19]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][CH2:22][N:21]([CH3:30])[C:20]1=[O:31]>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:18][CH:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][CH2:22][N:21]([CH3:30])[C:20]2=[O:31])=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acidHCID 210725651-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 102732871-(N'-(3,5-Difluorophenylacetyl)-L-alaninyl)amino 3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Procedure

Following General Procedure A above using N-(3,5-difluorophenylacetyl)-L-alanine (Example B) and 1-amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one, the title compound was prepared. The reaction was monitored by tlc on silica gel (Rf=0.15 in ethyl acetate) and purification was by flash chromatography using ethyl acetate as the eluant.

Workup

  1. customThe reaction was monitored by tlc on silica gel (Rf=0.15 in ethyl acetate) and purification

Sources & evidence

ORD record
ord-465a0d8a0fef428391f76a0c7468ed07
Source dataset
uspto-grants-2003_06
Patent number
US06579867B2

Reaction notes

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