Acetic Acid → Esomeprazole

HRID 1715717Notes

Reaction equation

HRID 1715717 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[N:6][C:7]([CH2:13][S+:14]([O-:26])[C:15]2[NH:16][C:17]3[CH:18]=[CH:19][C:20]([O:24][CH3:25])=[CH:21][C:22]=3[N:23]=2)=[C:8]([CH3:12])[C:9]=1[O:10][CH3:11].C1(C(C2C=CC=CC=2)(O)[C@H](C2C=CC=CC=2)O)C=CC=CC=1.C(O)(=O)C>C(O)C>[CH3:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([CH3:12])[C:7]([CH2:13][S@@:14]([C:15]2[NH:23][C:22]3[CH:21]=[C:20]([O:24][CH3:25])[CH:19]=[CH:18][C:17]=3[N:16]=2)=[O:26])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 7000031(2S)-1,1,2-Triphenyl-1,2-ethanediolHCID 178488147HCID 178488147, compound

Product 1

HCID 9568614Esomeprazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To aqueous sodium hydroxide (2.03 ml, 1.5 M, 3.04 mmol) at ambient temperature was added omeprazole (1 g, 2.90 mmol) in 5 portions over 10 min. On complete dissolution, ethanol (35 ml) and (S)-1,1,2-triphenyl-1,2-ethanediol (1.26 g, 4.34 mmol) were added. To the resulting colourless solution at ambient temperature was added a solution of aqueous acetic acid (3.04 ml, 1 M, 3.04 mmol) dropwise over 1 h and, on complete addition, stirring was continued for 4 h. The solid was filtered, was washed with ethanol (3×15 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (925 mg, 69%, 96.4% ee) as a white powder.

Workup

  1. additionwere added
  2. additionon complete addition
  3. filtrationThe solid was filtered
  4. washwas washed with ethanol (3×15 ml)
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-cda845a7afb14736a81c46fccebcd5db
Source dataset
uspto-grants-2010_09
Patent number
US07799925B2

Reaction notes

Loading…