Homoserine lactone hydrobromide → 3-(N'-(3,5-Difluorophenylacetyl)-L-alaninyl)-amino-gamma-butyrolactone

HRID 411317

Reaction equation

HRID 411317 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.Br.[NH2:19][CH:20]1[CH2:25][CH2:24][O:23][C:21]1=[O:22]>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([CH:25]2[CH2:24][O:23][C:21](=[O:22])[CH:20]2[NH2:19])=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 73508Homoserine lactone hydrobromideHCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid

Product 1

HCID 865849673-(N'-(3,5-Difluorophenylacetyl)-L-alaninyl)-amino-gamma-butyrolactone

Procedure

Following General Procedure A above using N-(3,5-difluorophenylacetyl)-L-alanine (Example B) and α-amino-γ-butyrolactone hydrobromide (Aldrich), the title compound was prepared as a solid having a melting point of 174-177° C. The reaction was monitored by tlc on silica gel (Rf=0.52 in 10% methanol/dichloromethane) and purification was by silica gel chromatography.

Workup

  1. customThe reaction was monitored by tlc on silica gel (Rf=0.52 in 10% methanol/dichloromethane) and purification

Sources & evidence

ORD record
ord-7c92c76fcf6340e381f63feea756c461
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Linked notes

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