Water → HCID 59383020, compound

HRID 2355468Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:15][CH2:14]1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][CH:13]1[CH2:14][CH2:15][CH:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[CH2:17][CH2:18]1)[CH2:10][O:11][S:35]([CH3:34])(=[O:37])=[O:36])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of (2S)-2-(t-butoxycarbonylamino)-3-(4-(t-butyldimethylsilyloxy)-cyclohexyl)propan-1-ol (23 g, 59 mmol) in CH2Cl2 (250 mL) was added Et3N (15 g, 148 mmol). The reaction mixture was cooled to −20° C. and a solution of MsCl (14.9 g, 131 mmol) in CH2Cl2 (40 mL) added dropwise. After returning to rt then stirring for an additional 1 h, at which point TLC showed no starting material, water (100 mL) was added and the mixture was extracted with CH2Cl2 (2×150 mL). The combined organic layers were washed with brine, dried over MgSO4 and evaporated to give crude (2S)-2-(t-butoxycarbonylamino)-3-(4-(t-butyldimethyl-silyloxy)cyclohexyl)-1-methanesulfonyloxypropane (30 g) that was used in the next step without further purification.

Workup

customAfter returning to rt
additionwas added
extractionthe mixture was extracted with CH2Cl2 (2×150 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-2967f6428ac5424ea27929f1d7fd8207
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754737B2

Reaction notes

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