Water → (S)-2-(tert-butoxycarbonylamino)-3-cyclopentylpropyl methanesulfonate

HRID 2355462Notes

Reaction equation

[CH:1]1([CH2:6][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>C(Cl)Cl>[CH:1]1([CH2:6][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:8][O:9][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

Crude tert-butyl (S)-3-cyclopentyl-1-hydroxypropan-2-ylcarbamate from the previous step was dissolved in CH2Cl2 (30 mL). Et3N (3.2 mL, 24.3 mmol) was added and the mixture was cooled to 0° C. A solution of MsCl (1.1 g, 9.7 mmol) in CH2Cl2 (10 mL) added dropwise. After stirring for an additional 2 h, water (30 mL) was added and the mixture was extracted with CH2Cl2 (2×30 mL). The combined organic layers were washed with brine, dried over MgSO4, and evaporated to give crude tert-butyl (S)-3-cyclopentyl-1-(methanesulfonyloxy)propan-2-ylcarbamate that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 1.09 (m, 2H), 1.46 (s, 9H), 1.50 (m, 3H), 1.60 (m, 3H), 1.81 (m, 3H), 3.02 (s, 3H), 3.86 (m, 1H), 4.17 (dd, J=10, 4 Hz, 1H), 4.27 (dd, J=10, 3.2 Hz, 1H), 4.59 (brs, 1H).

Workup

extractionthe mixture was extracted with CH2Cl2 (2×30 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-aeb14efd484f4c76ac66eeead96c1f33
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754737B2

Reaction notes

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