Triethylamine → HCID 178418975, compound

HRID 1366740Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11](=[O:20])[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl.C(=O)([O-])O.[Na+]>[C:6]([O:10][C:11]([NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]1)=[O:20])([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 2 °C

Procedure

Methanesulfonyl chloride (135 μl, 1.74 mmol) was added to a cooled (ice bath, 0-4° C.), stirred solution of trans-(4-hydroxycyclohexyl)carbamic acid tert-butyl ester (0.25 g, 1.16 mmol) and triethylamine (243 μl, 1.74 mmol) in dichloromethane (10 ml). Following the addition the reaction was stirred at this temperature for 30 minutes before being allowed to warm to ambient temperature. After stirring at ambient temperature for 2 hours, aqueous sodium hydrogen carbonate (10 ml) was added, followed by vigorous stirring for 30 minutes. The reaction was diluted with dichloromethane (20 ml) and aqueous sodium hydrogen carbonate (20 ml) and after partitioning the organic phase was washed with water (20 ml), dried (magnesium sulphate) and evaporated to dryness under reduced pressure to yield methanesulfonic acid trans-4-tert-butoxycarbonylaminocyclohexyl ester (340 mg, 100%).

Workup

additionthe addition the reaction
temperatureto warm to ambient temperature
stirringAfter stirring at ambient temperature for 2 hours
stirringby vigorous stirring for 30 minutes
customafter partitioning the organic phase
washwas washed with water (20 ml)
dry with materialdried (magnesium sulphate)
customevaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-96e754f71eee457cac1d2dacf2519df4
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893088B2

Reaction notes

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