(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → HCID 20640034, compound

HRID 636234Notes

Reaction equation

HRID 636234 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][C@@H:19]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:20]([OH:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23]>C(Cl)(Cl)Cl.CO>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:18][C@@H:19]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@@H:20]([OH:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acidHCID 14453007Methyl 4-amino-2,4,5-trideoxy-5-phenyl-L-threo-pentonate

Product 1

HCID 20640034HCID 20640034, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and methyl (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoate (Novabiochem), the title compound was prepared as a solid. The reaction was monitored by tlc (Rf=0.2 in 95:5 CHCl3/MeOH) and the product was purified by flash column chromatography using 95:5 CHCl3/MeOH as the eluent.

Workup

  1. customthe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-d044d72ba7d2449f89b70d838cc19e57
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Reaction notes

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