Toluene → [1,1'-Binaphthalene]-2,2'-diol, (1S)-, coMpd. with 5-Methoxy-2-[(S)-[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]sulfinyl]-1H-benziMidazole (1:1)

HRID 1952196Notes

Reaction equation

HRID 1952196 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].C1(C)C=CC=CC=1.[CH:32]1[CH:37]=[C:36]2[CH:38]=[CH:39][C:40]([OH:53])=[C:41]([C:42]3[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH:45]=[CH:44][C:43]=3[OH:52])[C:35]2=[CH:34][CH:33]=1>C1CCCCC1>[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.[CH:48]1[CH:47]=[C:46]2[CH:45]=[CH:44][C:43]([OH:52])=[C:42]([C:41]3[C:35]4[C:36](=[CH:37][CH:32]=[CH:33][CH:34]=4)[CH:38]=[CH:39][C:40]=3[OH:53])[C:51]2=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11762BinolHCID 178488147HCID 178488147, compound

Product 1

HCID 131730357[1,1'-Binaphthalene]-2,2'-diol, (1S)-, coMpd. with 5-Methoxy-2-[(S)-[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]sulfinyl]-1H-benziMidazole (1:1)Yield 85%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
52.5 °C

Procedure

Omeprazole (100 g, 0.2898 mole) was added to a mixture of toluene (1600 ml) and cyclohexane (400 ml) in a round bottom flask kept at 25-30° C. (S)-(−)-BINOL (124.3 g, 0.4346 mole) was added and the content warmed to about 50-55° C. with stirring for 30-45 minutes. The content of the flask was allowed to attain the ambient temperature and then cooled to 0-5° C. with stirring for about an hour. The (S)-omeprazole-(S)-(−)-BINOL complex crystallizes out, filtered and washed with a mixture of cyclohexane/toluene (1:4, v/v) pre-cooled to 0-5° C. The (S)-omeprazole-(S)-(−)-BINOL complex was dried at 35-40° C. under reduced pressure. The e.e. of (S)-omeprazole in the complex was found to be 99.5%. Yield: 85%.

Workup

  1. customkept at 25-30° C.
  2. additionwas added
  3. customthe ambient temperature
  4. temperaturecooled to 0-5° C.
  5. stirringwith stirring for about an hour
  6. customThe (S)-omeprazole-(S)-(−)-BINOL complex crystallizes out,
  7. filtrationfiltered
  8. washwashed with a mixture of cyclohexane/toluene (1:4, v/v)
  9. temperaturepre-cooled to 0-5° C
  10. customThe (S)-omeprazole-(S)-(−)-BINOL complex was dried at 35-40° C. under reduced pressure

Sources & evidence

ORD record
ord-1f67d0d3213d47a3999f94a07caf4fc9
Source dataset
uspto-grants-2013_03
Patent number
US08404853B2

Reaction notes

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