Dicyclohexylcarbodiimide → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(cyclopropyloxycarbonyl)-ethenyl]-cyclopropane-carboxylate

HRID 1995178Notes

Reaction equation

[CH:1]1([OH:4])[CH2:3][CH2:2]1.[CH3:5][C:6]1([CH3:33])[C@@H:8](/[CH:9]=[CH:10]\[C:11](O)=[O:12])[C@H:7]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].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:5][C:6]1([CH3:33])[C@@H:8](/[CH:9]=[CH:10]\[C:11]([O:4][CH:1]2[CH2:3][CH2:2]2)=[O:12])[C@H:7]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: 20 °C

Procedure

0.9 ml of cyclopropanol were added to a mixture of 5.5 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-carboxy-ethenyl]-cyclopropane-carboxylate in 26 ml of methylene chloride and 1 g of 4-dimethylamino-pyridine and 3 g of dicyclohexylcarbodiimide were added thereto at 0° C. The mixture was stirred at 20° C. for 90 minutes and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 85-15 cyclohexane-ethyl acetate mixture yielded 3.6 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(cyclopropyloxycarbonyl)-ethenyl]-cyclopropane-carboxylate melting at 62° C.

Workup

additionwere added
customat 0° C
filtrationwas filtered
customThe filtrate was evaporated to dryness under reduced pressure
customthe residue was chromatographed over silica gel
washElution with an 85-15 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-04979c34e91f441295f67515fa2701e9
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04402972

Reaction notes

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