Isobutanol → HCID 140656369, compound

HRID 2278377Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]([NH:24][S:25]([C:28]1[CH:36]=[CH:35][C:31]2[N:32]=[CH:33][S:34][C:30]=2[CH:29]=1)(=[O:27])=[O:26])[C:11]1[S:12][C:13](/[CH:16]=[N:17]\[S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:37](O)[CH:38]([CH3:40])[CH3:39].C(P(=CC#N)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][C@@H:10]([N:24]([CH2:37][CH:38]([CH3:40])[CH3:39])[S:25]([C:28]1[CH:36]=[CH:35][C:31]2[N:32]=[CH:33][S:34][C:30]=2[CH:29]=1)(=[O:27])=[O:26])[C:11]1[S:12][C:13](/[CH:16]=[N:17]\[S:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[O:19])=[CH:14][CH:15]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(5-{(Z)-[(tert-butylsulfinyl)imino]methyl}thiophen-2-yl)ethyl]-1,3-benzothiazole-6-sulfonamide (2.1 g, 3.58 mmol) and isobutanol (0.66 mL, 7.17 mmol) in toluene (18 mL) was added (tributyl-λ5-phosphanylidene)acetonitrile (1.74 mL, 7.17 mmol) and the reaction mixture was stirred at 100° C. for 2 hours. The mixture was cooled and then directly injected on a silica gel column eluting with hexanes and ethyl acetate.

Workup

temperatureThe mixture was cooled
washeluting with hexanes and ethyl acetate

Sources & evidence

ORD record: ord-c20780606db54c44af83b1dea6352d12
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133157B2

Reaction notes

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