Binol → Binol

HRID 1952194Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:24])[C:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=3[N:21]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].[CH:25]1[CH:30]=[C:29]2[CH:31]=[CH:32][C:33]([OH:46])=[C:34]([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][C:36]=3[OH:45])[C:28]2=[CH:27][CH:26]=1>>[CH:41]1[CH:40]=[C:39]2[CH:38]=[CH:37][C:36]([OH:45])=[C:35]([C:34]3[C:28]4[C:29](=[CH:30][CH:25]=[CH:26][CH:27]=4)[CH:31]=[CH:32][C:33]=3[OH:46])[C:44]2=[CH:43][CH:42]=1.[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S@@:12]([C:13]2[NH:21][C:20]3[CH:19]=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][C:15]=3[N:14]=2)=[O:24])=[N:4][CH:3]=1

Participants

Reactant 2

HCID 11762Binol

HCID 178488147HCID 178488147, compound

Product 2

HCID 11762Binol

HCID 9568614Esomeprazole

Procedure

In a later publication in Tetrahedron Asymmetry 11 (2000), 1729-1732 the inventors of the above mentioned Chinese patent application reported the resolution of omeprazole using (S)-BINOL. An inclusion complex of (S)-BINOL and (S)-omeprazole was obtained as a grey-blue complex with 90.3% e.e. by mixing racemate omeprazole and (S)-(−)-BINOL in the mole ratio 1:1.5, in a solvent mixture of benzene:hexane (v/v=4:1) at 110° C. The inclusion complex obtained was further purified by recrystallization in benzene:hexane (v/v, 1:1) and separated on a silica gel column to yield (S)-(−)-omeprazole with 98.9% e.e. and 84.1% overall yield. The (S)-(−)-omeprazole so obtained was recrystallized in water to obtain as a white powder with 99.2% e.e.

Sources & evidence

ORD record: ord-63a795a70abd4fab8abb974d8a4453f5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404853B2

Reaction notes

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