Triethylamine → (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate
Reaction equation
[C:1]([NH:8][C@@H:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:11][CH2:10][C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)(=[O:29])=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of (S)-N-Boc-2-amino-3-cyclohexylpropanol (20 g, 0.078 mol) in CH2Cl2 (400 mL) and triethylamine (19.6 g, 0.195 mol) was cooled to −20° C. Methanesulfonyl chloride (19.5 g, 0.171 mol) was added with fast dropwise addition maintaining the internal temperature at −20° C. The reaction mixture was stirred at −20° C. for an additional 30 min then for 1 h at 0° C. and then quenched with ice-cold water (200 mL). The mixture was extracted with CH2Cl2 (3×100 mL), washed with water (3×50 mL), dried over Na2SO4, concentrated to give the crude (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate (23.3 g, 90%), which was used for the next reaction without further purification. 1H NMR (400 MHz, CDCl3): 4.93 (m, 1H), 4.60 (d, J=7.6 Hz, 1H), 3.67 (m, 2H), 3.12 (s, 3H), 1.87-1.50 (m, 5H), 1.45 (s, 9H), 1.40-0.72 (m, 8H), MS (E/Z): 336 (M+H+).
Workup
- waitfor 1 h at 0° C.
- customquenched with ice-cold water (200 mL)
- extractionThe mixture was extracted with CH2Cl2 (3×100 mL)
- washwashed with water (3×50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c2bd4be44a0e45b49375e5e7c5e6ad84
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455521B2
Reaction notes
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