2-Methyl-2-butanol → HCID 56978820, compound

HRID 1995170Notes

Reaction equation

[CH3:1][C:2]1([CH3:31])[C@@H:4]([C:5]#[C:6][C:7](C(O)=O)=[O:8])[C@H:3]1[C:12]([O:14][C@H:15]([C:29]#[N:30])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)=[O:13].[C:32]([OH:37])([CH2:35][CH3:36])([CH3:34])[CH3:33].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:31])[C@@H:4]([C:5]#[C:6][C:7]([O:37][C:32]([CH2:35][CH3:36])([CH3:34])[CH3:33])=[O:8])[C@H:3]1[C:12]([O:14][C@H:15]([C:29]#[N:30])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)=[O:13]

Participants

Conditions

Temperature: 20 °C

Procedure

82 mg of 4-dimethylamino-pyridine were added with stirring at 5° C. to a mixture of 2.5 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[2-carboxycarbonyl-ethynyl]-cyclopropane-carboxylate, 12.5 ml of methylene chloride and 2.5 ml of tert.-amyl alcohol followed by the addition of 1.55 g of dicyclohexylcarbodiimide. The mixture was stirred at 20° C. for 41/2 hours and was cooled to 0° C. and filtered. The filtrate was evaporated to dryness under reduced pressure and was chromatographed over silica gel. Elution with an 8-2 cyclohexane-ethyl acetate mixture yielded 1.35 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[2-tert.-amyloxycarbonyl-ethynyl]-cyclopropane-carboxylate.

Workup

temperaturewas cooled to 0° C.
filtrationfiltered
customThe filtrate was evaporated to dryness under reduced pressure
customwas chromatographed over silica gel
washElution with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-666f8a165cad46f2a86d2dcba8de6886
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04402972

Reaction notes

Loading…