(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → 5-[N'-(3,5-Difluorophenylacetyl)-L-alaninyl]amino-7-(2-methylpropyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one

HRID 411360Notes

Reaction equation

HRID 411360 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.Cl.[NH2:19][N:20]1[C:26](=[O:27])[CH:25]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:24]2[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=2[C:22]2[CH:36]=[CH:37][CH:38]=[CH:39][C:21]1=2>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:19][N:20]2[C:26](=[O:27])[CH:25]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:24]3[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=3[C:22]3[CH:36]=[CH:37][CH:38]=[CH:39][C:21]2=3)=[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 222883145-Amino7-(2-methylpropyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one Hydrochloride

Product 1

HCID 102789255-[N'-(3,5-Difluorophenylacetyl)-L-alaninyl]amino-7-(2-methylpropyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one

Procedure

Following General Procedure D above using N-(3,5-difluorophenylacetyl)-L-alanine (Example B) and 5-amino-7-(2-methylpropyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one hydrochloride (Example 7-F), the title compound was prepared as a colorless solid. The product was purified by flash chromatography using 99:1 CHCl3/MeOH.

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-27dd979066bc42029c9b2a4d5aeaea1a
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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