Water → HCID 178488147, compound

HRID 425440Notes

Reaction equation

HRID 425440 reaction equation
C(Cl)Cl.O.[CH3:5][C:6]1[CH:7]=[N:8][C:9]([CH2:15][S+:16]([O-:28])[C:17]2[NH:18][C:19]3[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[CH:23][C:24]=3[N:25]=2)=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13].[Ca]>C(O)(=O)C>[CH3:5][C:6]1[CH:7]=[N:8][C:9]([CH2:15][S+:16]([O-:28])[C:17]2[NH:18][C:19]3[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[CH:23][C:24]=3[N:25]=2)=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 178488150HCID 178488150, compound

Product 1

HCID 178488147HCID 178488147, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
27.5 °C

Procedure

Methylene dichloride (130 ml) and water (65 ml) are added to enantiomerically pure esomeprazole calcium salt (13 gm, obtained in step-II) under stirring at 25-30° C., the contents are cooled to 15° C. and then pH of the mass is adjusted to 7.0-7.5 with acetic acid. The resulting mass is stirred for 15 minutes, separated the layers and the aqueous layer is extracted with methylene dichloride (100 ml). The total organic layer is washed with 5% NaCl solution (65 ml), dried over sodium sulfate and the resulting organic layer is distilled under vacuum at 40° C. and then co-distilled with methanol (100 ml) to give 10.3 gm of enantiomerically pure esomeprazole as residue (enantiomeric purity: 100%).

Workup

  1. temperaturethe contents are cooled to 15° C.
  2. stirringThe resulting mass is stirred for 15 minutes
  3. customseparated the layers
  4. extractionthe aqueous layer is extracted with methylene dichloride (100 ml)
  5. washThe total organic layer is washed with 5% NaCl solution (65 ml)
  6. dry with materialdried over sodium sulfate
  7. distillationthe resulting organic layer is distilled under vacuum at 40° C.

Sources & evidence

ORD record
ord-0c382b573f7d49e992ab6097ba3d2ffb
Source dataset
uspto-grants-2012_01
Patent number
US08106210B2

Reaction notes

Loading…