Dimethyl acetylenedicarboxylate → HCID 73743288, compound

HRID 1767116Notes

Reaction equation

HRID 1767116 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:14]([NH2:17])=[N:15][OH:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21]([C:23]#[C:24][C:25]([O:27][CH3:28])=[O:26])=[O:22]>C(Cl)(Cl)Cl>[CH3:19][O:20][C:21](=[O:22])[C:23]([O:16][N:15]=[C:14]([NH2:17])[C:8]1([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:18])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)=[CH:24][C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 73743302519031-88-0

Product 1

HCID 73743288HCID 73743288, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl-4-[amino(hydroxyimino)methyl]tetrahydro-2H-pyran-4-yl-carbamate (C-27) 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=7:3) to give the desired product (C-28) as a mixture of isomers in ratio 7:3.

Workup

  1. concentrationthe solution was concentrated
  2. customResidue was purified by flash chromatography on silica gel (eluent:petroleum ether:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-d130e113ba814c408c95d20e3667bac3
Source dataset
uspto-grants-2007_06
Patent number
US07232819B2

Reaction notes

Loading…