Ethyl 7-chloro-2-oxoheptanoate → ethyl (E)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate

HRID 2222779Notes

Reaction equation

HRID 2222779 reaction equation
ClCCCCCC(=O)C(OCC)=O.CC1(C)C[C@@H]1C(N)=O.[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[C:28](\[NH:34][C:35]([C@H:37]1[CH2:39][C:38]1([CH3:41])[CH3:40])=[O:36])/[C:29]([O:31][CH2:32][CH3:33])=[O:30]>>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[C:28](/[NH:34][C:35]([C@H:37]1[CH2:39][C:38]1([CH3:40])[CH3:41])=[O:36])\[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

4

Reactant 3

HCID 3018793Ethyl 7-chloro-2-oxoheptanoateHCID 10197657(S)-2,2-DimethylcyclopropanecarboxamideHCID 57734487ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate

Product 1

HCID 67298182ethyl (E)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoateYield 10.5%

Procedure

As described in European Patent No. 48301, 250 g of ethyl 7-chloro-2-oxoheptanoate and 141 g of (S)-2,2-dimethyl cyclopropanecarboxamid were reacted and concentrated. In result, 372.4 g of ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-hepnoate (2) containing, by gas chromatography assay, 10.5% of ethyl (E)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (3) was obtained.

Workup

  1. concentrationconcentrated
  2. customIn result

Sources & evidence

ORD record
ord-7893dcc369ee4b42a2f14bfca804083c
Source dataset
uspto-grants-2008_05
Patent number
US07371897B1

Reaction notes

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