Sodium Hydroxide → HCID 178488147, compound

HRID 453672Notes

Reaction equation

HRID 453672 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].C1C=CC2C(C3C(O)=CC=C4C=3C=CC=C4)=C(O)C=CC=2C=1.[OH-].[Na+]>C(OC)(C)(C)C>[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]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178488158Esomeprazole BINOL

Product 1

HCID 178488147HCID 178488147, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Esomeprazole-BINOL inclusion complex (100 g; 158.29 mmol; ee of 98.28%) was suspended in methyl t-butyl ether (1300 ml). Aqueous sodium hydroxide solution (2.2% w/w; 302 g) was added to the suspended mass at 20-30° C. and stirred till clear solution was obtained. Thereafter, organic layer was separated and the aqueous layer was extracted with methyl t-butyl ether for recovery of BINOL. The organic layers were combined, concentrated and recovered 44.4 g of BINOL. To the aqueous layer, methylene chloride (300 ml) was added and pH was adjusted to 7-8 with 10% v/v aqueous acetic acid. The organic layer was separated and washed with DM water and concentrated under reduced pressure to yield esomeprazole as a foamy solid mass.

Workup

  1. customwas obtained
  2. customThereafter, organic layer was separated
  3. extractionthe aqueous layer was extracted with methyl t-butyl ether for recovery of BINOL
  4. concentrationconcentrated
  5. customrecovered 44.4 g of BINOL
  6. additionTo the aqueous layer, methylene chloride (300 ml) was added
  7. customThe organic layer was separated
  8. washwashed with DM water
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cde4a1f00bf740c79c04cb230bec1eb0
Source dataset
uspto-grants-2013_07
Patent number
US08492551B2

Reaction notes

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