Dimethyl acetylenedicarboxylate → HCID 86609166, compound

HRID 2114786Notes

Reaction equation

HRID 2114786 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][CH3:17])[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.[C:22]([C:28]([O:30][CH3:31])=[O:29])#[C:23][C:24]([O:26][CH3:27])=[O:25]>C(Cl)(Cl)Cl>[CH3:27][O:26][C:24](=[O:25])[C:23]([O:20][N:19]=[C:18]([NH2:21])[C@@H:12]1[CH2:13][C@@H:14]([O:16][CH3:17])[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:22][C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 86609165HCID 86609165, compound

Product 1

HCID 86609166HCID 86609166, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To benzyl-(2S,4R)-2-[amino(hydroxyimino)methyl]-4methoxypyrrolidine-1-carboxylate, dissolved in chloroform, dimethyl acetylendicarboxylate (1.1 eq.) was added. The mixture was refluxed for 1 hour and left stirring at 40° C. overnight. The chloroform was removed in vacuo and the crude product purified by flash chromatography on silica gel (eluent ethyl acetate:petroleum ether=40:60). Two isomers were present in ratio 7:3.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. waitleft
  3. customThe chloroform was removed in vacuo
  4. customthe crude product purified by flash chromatography on silica gel (eluent ethyl acetate:petroleum ether=40:60)

Sources & evidence

ORD record
ord-7391c64ddf5d4f50b1888c26e6311313
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

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