Triethylamine → HCID 90238121, compound

HRID 2207108Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:13]([OH:24])[C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([O:24][CH:13]([C:5]1[CH:4]=[C:3]([C:2]([F:25])([F:26])[F:1])[CH:8]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:6]=1)[C@@H:14]([NH:16][C:17]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:23])[CH3:15])(=[O:37])=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl ((2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-yl)carbamate (2.0 g, 5.16 mmol) and triethylamine (1.15 ml, 8.26 mmol) at 0° C. in DCM (20 ml) was added methanesulfonyl chloride (0.48 ml, 6.2 mmol). The reaction was stirred at 0° C. for 1 hour and then was quenched with a saturated solution of NH4Cl. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated. The product was purified by column chromatography to yield (2S)-1-(3,5-bis(trifluoromethyl)phenyl)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate. The crude material was judged to have a 9:1 diastereomeric ratio by 1H NMR analysis. 1H NMR (500 MHz, CDCl3): δ 7.91 (s, 1H); δ 7.87 (s, 0.1H); δ 7.84 (s, 2H); 5.73 (d, J=4.3 Hz, 1H); δ 5.21 (d, J=7.0 Hz, 0.1H); δ 4.58 (s, 1H); 4.18 (br s, 1H); 3.02 (s, 3H); 1.39 (s, 9H); 1.25 (d, J=6.9 Hz, 3H).

Workup

customwas quenched with a saturated solution of NH4Cl
washThe organic layer was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-a2955287ffdc4034a094fa45c581a63e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376408B2

Reaction notes

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