Dimethyl acetylenedicarboxylate → HCID 86609164, compound

HRID 1375554Notes

Reaction equation

HRID 1375554 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([F:16])[CH2:13][C@H:12]1[C:17]([NH2:20])=[N:18][OH:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]([C:25]#[C:26][C:27]([O:29][CH3:30])=[O:28])=[O:24]>C(Cl)(Cl)Cl>[CH3:21][O:22][C:23](=[O:24])[C:25]([O:19][N:18]=[C:17]([NH2:20])[C@@H:12]1[CH2:13][C@H:14]([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:26][C:27]([O:29][CH3:30])=[O:28]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 86609163HCID 86609163, compound

Product 1

HCID 86609164HCID 86609164, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Benzyl-(2S,4S)-2-[amino(hydroxyimino)methyl]-4-fluoropyrrolidine-1-carboxylate in chloroform was treated with dimethylacetylene dicarboxylate for 3 hours at 60° C. The chloroform was then concentrated to give the title compound as a 8:2 mixture of isomers.

Workup

  1. concentrationThe chloroform was then concentrated

Sources & evidence

ORD record
ord-f6b04d155fc64364a45c3358b1dc2bd1
Source dataset
uspto-grants-2007_01
Patent number
US07169780B2

Reaction notes

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