NADPH → 1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol

https://huagongshe.com/reaction/1972413

Participants

Role	Name	HCID	Charge
Reactant	NADPH	HCID 5884	—
Reactant	1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol	HCID 66582832	—
Reactant	1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol	HCID 66583110	—
Reactant	1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol	HCID 70656371	—
Product	1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol	HCID 66582453	—

Reaction Steps

1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol; 1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol; 1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-azetidinol. 1H NMR (400 MHz, DMSO-d6) δ 8.08-8.06 (m, 1H), 7.68-7.66 (m, 1H), 7.40-7.38 (d, J=9.2 Hz, 2H), 7.31-7.29 (m, 1H), 6.86-6.84 (d, J=9.2 Hz, 2H), 4.14-4.10 (m, 1H), 3.44-3.38 (m, 4H), 3.06-2.99 (m, 1H), 2.88-2.82 (m, 1H), 2.73-2.70 (m, 1H), 2.57-2.53 (m, 2H), 2.48-2.38 (m, 3H), 2.07-2.04 (m, 1H), 1.62 (s, 3H). m/z (ESI, +ve ion) 506.2 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=2.26 μM; GK-GKRP EC50 (LC MS/MS)=1.79 μM.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08431563B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-a40ceaf493ab48418852c339c8136c50
Source note	uspto-grants-2013_04