Iodoethane → HCID 86630136, compound

HRID 656215Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([S:14][CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C@@H:9]1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])([CH3:4])([CH3:3])[CH3:2].[CH2:34](I)[CH3:35]>>[C:1]([O:5][C:6](=[O:33])[N:7]([C@@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([S:14][CH2:15][C:16]2[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])[C@@H:9]1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[CH2:34][CH3:35])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 6340Iodoethane

HCID 86630137HCID 86630137, compound

Product 1

HCID 86630136HCID 86630136, compound

Procedure

A solution of [(1R,2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(2,4,6-trimethyl-benzylsulfanyl)-cyclohexyl]-carbamic acid tert-butyl ester+(1S,2S,3S) diastereomer (3.0 g, 6.08 mmol) was treated with ethyl iodide according to the method of Example 7 Step A. After work up and chromatography of the reaction mixture (silica, cyclohexane/ethyl acetate=3/1) [(1R,2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(2,4,6-trimethyl-benzylsulfanyl)-cyclohexyl]-ethyl-carbamic acid tert-butyl ester+(1S,2S,3S) diastereomer (1.20 g, 38%) was obtained.

Sources & evidence

ORD record: ord-566db8567aa04cfdabfd42b5c78eed30
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071643B2

Reaction notes

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