(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → HCID 22894863, compound

HRID 322765Notes

Reaction equation

HRID 322765 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]([C:24]1[S:25][C:26]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:27]=2[CH:28]=1)[C:20]([O:22][CH3:23])=[O:21].ClC1C=CC2SC(CC(O)=O)=CC=2C=1>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:18][CH:19]([C:24]2[S:25][C:26]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:27]=3[CH:28]=2)[C:20]([O:22][CH3:23])=[O:21])=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 3

HCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acidHCID 22492001HCID 22492001, compoundHCID 22492125HCID 22492125, compound

Product 1

HCID 22894863HCID 22894863, compound

Procedure

Following General Procedure C and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and methyl 2-amino-2-(5-chlorobenzothiophen-2-yl)acetate (prepared from 5-chlorobenzothiophene-2-acetic acid [CAS No. 23799-65-7] using General Procedure G, followed by amination using a procedure essentially the same as that described in Example D4 above), the title compound was prepared as a solid (mp=189-190° C.). The product was purified by titration using Et20/hexanes.

Sources & evidence

ORD record
ord-16510128ede1434196ff4cc45d107aae
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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