Diazomethane → HCID 86739802, compound

HRID 1383194Notes

Reaction equation

[N+](=[CH2:3])=[N-].[CH3:4][C:5]1([CH3:33])[C@H:7](/[CH:8]=[C:9](/[F:13])\[C:10](=[O:12])[OH:11])[C@H:6]1[C:14]([O:16][C@H:17]([C:31]#[N:32])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)=[O:15]>C(Cl)Cl.C(O)(=O)C>[CH3:4][C:5]1([CH3:33])[C@H:7](/[CH:8]=[C:9](/[F:13])\[C:10](=[O:11])[O:12][CH3:3])[C@H:6]1[C:14]([O:16][C@H:17]([C:31]#[N:32])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)=[O:15]

Participants

Conditions

Temperature: 5 °C

Procedure

A slight excess of diazomethane in methylene chloride solution was added at 5° to 10° C. to a solution of 860 mg of the product of Step A in 2 ml of methylene chloride and the mixture was stirred at 5° C. for 15 minutes and at room temperature for 30 minutes. A few drops of acetic acid were added to the mixture which was then evaporated to dryness to obtain 950 mg of an oil residue. The latter was chromatographed over silica gel and was eluted with an 85-15 hexane-ethyl acetate mixture to obtain 700 mg of (S)α-cyano-3-phenoxy-benzyl (1R, trans) 2,2-dimethyl-3(E)-[2-fluoro-3-oxo-3-methoxy-propenyl]-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =-31°±2.5° (c=0.25% in chloroform).

Workup

customwas then evaporated to dryness

Sources & evidence

ORD record: ord-56659c92db0b4e9ea80ae53fc7bde629
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808749

Reaction notes

Loading…