(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → HCID 20604345, compound

HRID 480772Notes

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][CH:20]1[CH2:26][C:25]([CH3:28])([CH3:27])[CH:24]=[N:23][C:22]2[CH:29]=[CH:30][CH:31]([CH3:34])[C:32](=O)[C:21]1=2.C[OH:36].C(Cl)(Cl)Cl>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:19][CH:20]2[C:26](=[O:36])[C:25]([CH3:28])([CH3:27])[CH:24]=[N:23][C:22]3[CH:29]=[CH:30][CH:31]([CH3:34])[CH2:32][C:21]2=3)=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

Reactant 3

HCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid

HCID 21584188Chloroform methanol

HCID 22312448HCID 22312448, compound

Product 1

HCID 20604345HCID 20604345, compound

Procedure

Following General Procedure D and using N-(3,5-difluorophenylacetyl)-L-alanine (Ex. B) and 5-amino-3,3,7-trimethyl-5,7-dihydro-6H-benz[b]azepin-6-one hydrochloride (Example 6-C), the title compound was prepared. The reaction was monitored by tlc (Rf=0.4, 5% MeOH/CHCl3) and product was purified by chromatography (silica, 5% MeOH/CHCl3) and crystallization from acetonitrile.

Workup

customwas purified by chromatography (silica, 5% MeOH/CHCl3) and crystallization from acetonitrile

Sources & evidence

ORD record: ord-a5acc153cb7442bd9e32402c48239ad1
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653303B1

Reaction notes

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