Triethylamine → 2-(Benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate

HRID 451788Notes

Reaction equation

[OH:1][CH2:2][CH:3]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:4][C:5]1([CH3:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:1][CH2:2][CH:3]([NH:12][C:13]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:22])[CH2:4][C:5]1([CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)(=[O:33])=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 0.3607 g (1.18 mmol) of benzyl 1-hydroxy-3-(1-methylcyclohexyl)propan-2-ylcarbamate, 0.4 mL (2.87 mmol, 2.43 equiv) of triethylamine, 0.1 mL (1.29 mmol, 1.09 equiv) of methanesulfonyl chloride in CH2Cl2 (10 mL) was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with ice water, extracted with CH2Cl2, washed with aqueous NaHCO3, and dried over Na2SO4. After the solvent was removed in vacuo, the crude 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate was used directly in the next step without further purification. MS ESI +ve m/z 406 (M+Na).

Workup

customThe reaction mixture was quenched with ice water
extractionextracted with CH2Cl2
washwashed with aqueous NaHCO3
dry with materialdried over Na2SO4
customAfter the solvent was removed in vacuo
customthe crude 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate was used directly in the next step without further purification

Sources & evidence

ORD record: ord-955a3d1e77ea42498895707e1b154213
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

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