Acetonitrile → HCID 178500939, compound

HRID 2219051Notes

Reaction equation

HRID 2219051 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[N:8][OH:9].C(#N)C.[C:13]([C:19]([O:21][CH3:22])=[O:20])#[C:14][C:15]([O:17][CH3:18])=[O:16]>>[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[N:8][O:9]/[C:14](=[CH:13]/[C:19]([O:21][CH3:22])=[O:20])/[C:15]([O:17][CH3:18])=[O:16].[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[N:8][O:9]/[C:14](=[CH:13]\[C:19]([O:21][CH3:22])=[O:20])/[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 12980Dimethyl acetylenedicarboxylateHCID 178526316HCID 178526316, compound

Product 2

HCID 178500939HCID 178500939, compoundHCID 178500940HCID 178500940, compound

Procedure

To a suspension of azepan-2-one oxime in acetonitrile 1.1 eq. of dimethyl acetylenedicarboxylate were added dropwise under stirring. The mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure to afford a mixture 8/1 of dimethyl (2E)-2-[(azepan-2-ylideneamino)oxy]but-2-enedioate and dimethyl (2Z)-2-[(azepan-2-ylideneamino)oxy]but-2-enedioate as a yellow oil. To better characterize the title compounds a small amount of the crude was purified by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluents (column C18). The pooled product fractions were lyophilized.

Workup

  1. additionwere added dropwise
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e744fddea72249e4b0931e7b1537ac94
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

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