Dicyclohexylcarbodiimide → HCID 53910544, compound

HRID 485711Notes

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:32])[C@H:19]([CH:20]=[C:21]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23])[C@H:18]1[C:29]([OH:31])=[O:30].[C:33]([C@@H:35](O)[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:37]=1)#[N:34]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:32][C:17]1([CH3:16])[C@H:19]([CH:20]=[C:21]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23])[C@H:18]1[C:29]([O:31][C@H:35]([C:33]#[N:34])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:37]=1)=[O:30]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 1.3 g of dicyclohexylcarbodiimide and 30 mg of 4-dimethylamino-pyridine in 15 ml of dichloromethane were added to a solution of 1.5 g of the product of Step E, 1.42 g of (S)α-cyano-3-phenoxy-benzyl alcohol and 30 ml of dichloromethane and the mixture was stirred at 20° C. for 18 hours and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 4-1 hexane-ethyl acetate mixture yielded 1.16 g of (S)α-cyano-3-phenoxy-benzyl (1R,trans) 2,2-dimethyl-3-(3-ethoxycarbonyl-1,2-butadienyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+35° (chloroform).

Workup

filtrationwas filtered
customThe filtrate was evaporated to dryness under reduced pressure
customthe residue was chromatographed over silica gel
washElution with a 4-1 hexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-e359560606bf43e397b13f2f872ed2d4
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04537897

Reaction notes

Loading…