Triethylamine → (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate
Reaction equation
[F:1][C:2]1([CH2:8][C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][OH:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[CH3:20][S:21]([O:11][CH2:10][C@@H:9]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[CH2:8][C:2]1([F:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)(=[O:23])=[O:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (275 mg, 1.0 mmol, 1.0 equiv) was dissolved in CH2Cl2 and the mixture was cooled to 0° C. To this solution was added methanesulfonyl chloride (230 mg, 2.0 mmol, 2.0 equiv) and triethylamine (304 mg, 3.0 mmol, 3.0 equiv). The mixture was stirred at 0° C. for 0.5 h. After this time LC/MS showed consumption of the starting material. The mixture was transferred to a separatory funnel and 1.0 M aq HCl added. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The crude (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate was used directly in the next step.
Workup
- customconsumption of the starting material
- customThe mixture was transferred to a separatory funnel
- addition1.0 M aq HCl added
- customThe layers were separated
- washthe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-604bc6bda47947ecb0b6af8f3262fd91
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487108B2
Reaction notes
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