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

HRID 451780Notes

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.[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>C(Cl)Cl>[CH3:18][S:19]([O:9][CH2:8][C@@H:7]([NH:10][C:11]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:17])[CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

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

Workup

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

Sources & evidence

ORD record: ord-7aa49efc84c8464c9f0dd8f29e78f5e5
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

Loading…