(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → HCID 22894913, compound

HRID 322705Notes

Reaction equation

HRID 322705 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.[C:19]([O:23][C:24](=[O:31])[C@H:25]([CH2:27][CH2:28][CH2:29][CH3:30])[NH2:26])([CH3:22])([CH3:21])[CH3:20]>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:26][C@@H:25]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24]([O:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:31])=[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 86590451Norleucine tert-butyl ester hydrochloride

Product 1

HCID 22894913HCID 22894913, compound

Procedure

Following General Procedure D and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and the norleucine tert-butyl ester hydrochloride, the title compound was prepared as a semi-solid. The reaction was monitored by tlc (Rf=0.41 in 50% EtOAc/hexanes) and the product was purified by flash chromatography using 50% EtOAc/hexanes as the eluent, followed by preparative plate chromatography using 50% EtOAc/hexanes as the eluent.

Workup

  1. customthe product was purified by flash chromatography

Sources & evidence

ORD record
ord-8384a1617ffa475bad7461db77530898
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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