Toluene → Esomeprazole BINOL

HRID 404609

Reaction equation

HRID 404609 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].[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1CCCCC1>[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:28]1[CH:29]=[C:30]2[CH:1]=[CH:2][C:7]([OH:8])=[C:31]([C:19]3[C:20]4[C:15](=[CH:11][CH:5]=[CH:6][CH:10]=4)[CH:16]=[CH:17][C:18]=3[OH:22])[C:25]2=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 178488147HCID 178488147, compound

Product 1

HCID 178488158Esomeprazole BINOL

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
52.5 °C

Procedure

S-1,1′-bi-2-naphthol (124 gm) was added to a solution of omeprazole (100 gm) in a mixture of toluene and cyclohexane (2000 ml, 4:1) at room temperature. The reaction mixture was heated to 50 to 55° C. and maintained for 1 hour at 50 to 55° C. The solution was cooled to room temperature and filtered, washed with a mixture of toluene and cyclohexane (200 ml, 4:1). The solid was dried at 45 to 50° C. under vacuum for 4 hours to obtain 80 gm of esomeprazole-S-BINOL complex.

Workup

  1. temperaturemaintained for 1 hour at 50 to 55° C
  2. temperatureThe solution was cooled to room temperature
  3. filtrationfiltered
  4. washwashed with a mixture of toluene and cyclohexane (200 ml, 4:1)
  5. customThe solid was dried at 45 to 50° C. under vacuum for 4 hours
  6. customto obtain 80 gm of esomeprazole-S-BINOL complex

Sources & evidence

ORD record
ord-5282e32539d5421fbaf390c21fe79494
Source dataset
uspto-grants-2014_06
Patent number
US08748619B2

Linked notes

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