Dimethyl acetylenedicarboxylate → Dimethyl-2-{[(amino-{(2S)-1-[(benzyloxy)carbonyl]-4,4-difluoropyrrolidin-2-yl}methylidene)amino]oxy}but-2-enedioate

HRID 1161939Notes

Reaction equation

HRID 1161939 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][C@H:12]1[C:18]([NH2:21])=[N:19][OH:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]([C:26]#[C:27][C:28]([O:30][CH3:31])=[O:29])=[O:25]>C(Cl)(Cl)Cl>[CH3:22][O:23][C:24](=[O:25])[C:26]([O:20][N:19]=[C:18]([NH2:21])[C@@H:12]1[CH2:13][C:14]([F:17])([F:16])[CH2:15][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[CH:27][C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 86609167Benzyl-(2S)-2-[amino(hydroxyimino)methyl]4,4-difluoropyrrolidine-1-carboxylate

Product 1

HCID 86624401Dimethyl-2-{[(amino-{(2S)-1-[(benzyloxy)carbonyl]-4,4-difluoropyrrolidin-2-yl}methylidene)amino]oxy}but-2-enedioate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of benzyl-(2S)-2-[amino(hydroxyimino)methyl]-4,4-difluoropyrrolidine-1-carboxylate and dimethylacetylendicarboxylate (1.2 eq.) in chloroform was refluxed for 1 hour under nitrogen and the solution was concentrated. Residue was purified by flash chromatography on silica gel, (eluent: petroleum ether:ethyl acetate=7.5:2.5), to give the desired product as a 3:1 mixture of two isomers by 1H NMR.

Workup

  1. concentrationthe solution was concentrated
  2. customResidue was purified by flash chromatography on silica gel, (eluent: petroleum ether:ethyl acetate=7.5:2.5),

Sources & evidence

ORD record
ord-9c1a3bcf7e834cc8aa6ade6c479683dc
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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