Triethylamine → HCID 21048948, compound

HRID 2212367Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][CH:23]([OH:25])[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C(OCC)(=O)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:12][CH2:13][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][CH:23]([O:25][S:42]([CH3:41])(=[O:44])=[O:43])[CH2:22]3)(=[O:19])=[O:20])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1-[4-(4-chloro-benzenesulfonyl)-4-(2,5-difluoro-phenyl)-cyclohexylmethanesulfonyl]-azetidin-3-ol (Example 30) (180 mg, 0.35 mmol) in dichloromethane (10 mL) at 0° C. was added triethylamine (0.08 mL, 0.58 mmol) and methanesulfonyl chloride (0.035 mL, 0.45 mmol) and the mixture stirred 2 hours at 0° C. Ethyl acetate (20 mL) was added and the mixture washed with 2N aqueous hydrochloric acid (20 μL) and brine (20 mL), dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica, eluting with ethyl acetate:iso-hexane (1:1), to afford the desired product (162 mg).

Workup

washthe mixture washed with 2N aqueous hydrochloric acid (20 μL) and brine (20 mL)
dry with materialdried (MgSO4)
customevaporated
customto leave a residue which
customwas purified by column chromatography on silica
washeluting with ethyl acetate:iso-hexane (1:1)

Sources & evidence

ORD record: ord-051319df5181437b8c6ffbe4f1ec7116
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101895B2

Reaction notes

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