Triethylamine → (+/-)-Methanesulfonic acid 2-[(2-benzyloxy-5-fluoro-phenyl)-methanesulfonyloxy-methyl]-benzyl ester

HRID 2036237Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][OH:25])[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[CH:16]([O:17][S:34]([CH3:33])(=[O:36])=[O:35])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][O:25][S:34]([CH3:33])(=[O:36])=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cooled solution of (±)-(2-benzyloxy-5-fluoro-phenyl)-(2-hydroxymethyl-phenyl)-methanol (500 mg, 1.48 mmol, 1.00 eq.) and DMAP (9 mg, 0.07 mmol, 0.05 eq.) in DCM (30 mL), NEt3 (0.82 mL, 5.91 mmol, 4.00 eq.) and methanesulfonyl chloride (0.24 mL, 3.10 mmol, 2.10 eq.) were added dropwise. The mixture was stirred at 0° C. for 1 hour and further at r.t. for 2 hours. The reaction mixture was diluted with H2O (50 mL) and DCM (50 mL). The layers were separated. The aq. phase was extracted with DCM (2×50 mL). The comb. org. phases were washed with water (1×150 mL), sat. aq. NaCl soln. (1×50 mL), dried over MgSO4, and concentrated in vacuo to give (±)-methanesulfonic acid 2-[(2-benzyloxy-5-fluoro-phenyl)-methanesulfonyloxy-methyl]-benzyl ester.

Workup

additionwere added dropwise
customThe layers were separated
extractionThe aq. phase was extracted with DCM (2×50 mL)
washphases were washed with water (1×150 mL), sat. aq. NaCl soln
dry with material(1×50 mL), dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8fb8d60eee3a4487a028808cc4f4beec
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575158B2

Reaction notes

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