Triethylamine → (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate

HRID 1254215Notes

Reaction equation

[CH:1]1([CH2:7][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:10][CH2:9][C@@H:8]([NH:11][C:12]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:18])[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)(=[O:29])=[O:28]

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of tert-butyl (S)-3-cyclohexyl-1-hydroxypropan-2-ylcarbamate (3.02 g, 11.7 mmole) in CH2Cl2 (50 mL) and triethylamine (4.0 mL, 28.6 mmol) was cooled to −20° C. (internal temperature). Neat methanesulfonyl chloride (2.0 mL, 25.7 mmol) was added dropwise, maintaining the internal temperature at −20° C. (+/−5° C.). The reaction mixture was stirred at −20° C. for an additional 30 min and at 0° C. for 1 h. Reaction progress was followed by TLC and LC-MS. The reaction was quenched with ice-cold water, extracted with CH2Cl2 (3×20 mL), washed with water (3×10 mL), dried (Na2SO4), decanted, and stripped to give 4.13 g (quant) of product. 1H NMR (CDCl3) δ 0.80-1.40 (10H), 1.40 (s, 9H), 1.65 (t, 2H), 1.75 (d, 1H), 2.95 (s, 3H), 3.94 (m, 1H), 4.10 (m, 1H), 4.24 (m, 1H), 4.60 (m, 1H). MS ESI +ve m/z 236 (M(−BOC)+1).

Workup

customReaction progress
customThe reaction was quenched with ice-cold water
extractionextracted with CH2Cl2 (3×20 mL)
washwashed with water (3×10 mL)
dry with materialdried (Na2SO4)
customdecanted
customto give 4.13 g (quant) of product

Sources & evidence

ORD record: ord-d4dd8f7990f54eaebb845ec8525fbf35
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455521B2

Reaction notes

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