Triethylamine → HCID 68581004, compound

HRID 2235831Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=1[CH2:25]O)([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[OH:9].C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:17]2[C:18](=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=2)[CH2:25][O:9]1

Participants

Conditions

Temperature: 7.5 °C

Procedure

4-[3-[1, 3]-Dioxolan-2-yl-1-(4-fluorophenyl)-1-hydroxypropyl-]3-hydroxymethylbenzonitrile (15 g) was dissolved in dichloromethane (150 mL) at room temperature, followed by addition of triethylamine (25 mL). The reaction mixture was cooled to 5-10° C. and stirred for 5 min, followed by addition of methane sulfonylchloride (8.4 g). The reaction mixture was warmed to room temperature and stirred for 10 min. It was quenched with 2% NaOH (100 mL) while maintained to 10-20° C. The organic phase was separated and was dissolved in water and concentrated to give 19.2 g crude product. 1H NMR (CDCl3, δ): 1.42-1.57 (m, 1H), 1.63-1.76 (m, 1H), 2.20-2.38 (m, 2H), 3.78-3.96 (m, 4H), 4.84 (t, J=3 Hz, 1H), 5.18 (m, 2H), 7.00 (m, 2H), 7.38-7.50 (m, 4H), 7.60 (m, 1H). The product was separated into its enantiomers by CHIRALCEL OD=column using Methanol as eluent. Enantiomer 6a, 6.67 min; Enantiomer 6b, 8.30 min.

Workup

temperatureThe reaction mixture was warmed to room temperature
stirringstirred for 10 min
customIt was quenched with 2% NaOH (100 mL)
temperaturewhile maintained to 10-20° C
customThe organic phase was separated
dissolutionwas dissolved in water
concentrationconcentrated

Sources & evidence

ORD record: ord-6c29f50ce389419894334f117f46b21d
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714023B2

Reaction notes

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