(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → Methyl 1-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]piperidine-2-carboxylate

HRID 322785Notes

Reaction equation

HRID 322785 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.[NH:19]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:20]1[C:21]([O:23][CH3:24])=[O:22]>CO.C(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([N:19]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:20]2[C:21]([O:23][CH3:24])=[O:22])=[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 13246231Methyl Pipecolinate Hydrochloride

Product 1

HCID 9842199Methyl 1-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]piperidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following General Procedure A and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and methyl pipecolinate hydrochloride (Aldrich), the title compound was prepared as a solid (mp=114-118° C.). The reaction was monitored by tlc (Rf=0.71 in 10% MeOH/DCM) and the product was purified by acid/base washes.

Workup

  1. customthe product was purified by acid/base washes

Sources & evidence

ORD record
ord-1269bb1bc3eb4b3496d34f90ffc02e15
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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