(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → HCID 10111896, compound

HRID 322726Notes

Reaction equation

HRID 322726 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:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>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][CH:19]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[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 14980462HCID 14980462, compound

Product 1

HCID 10111896HCID 10111896, 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 ethyl 2-amino-2-(3-pyridyl)acetate (prepared as described in P. Kolar et al., J Heterocyclic Chem., 28, 1715 (1991) and references cited therein), the title compound was prepared as a solid (mp=146-157° C.). The reaction was monitored by tlc (Rf=0.1 in CHCl3/MeOH 98:2) and the product was purified by silica gel chromatography using 959:5 CHCl3/MeOH as the eluent, followed by recrystallization from chlorobutane.

Workup

  1. customprepared
  2. customthe product was purified by silica gel chromatography
  3. customfollowed by recrystallization from chlorobutane

Sources & evidence

ORD record
ord-45c0571b3cee423fa061cc15ebdbbf76
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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