(2S)-1,1,2-Triphenyl-1,2-ethanediol → Esomeprazole

HRID 1715714Notes

Reaction equation

HRID 1715714 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(C2C=CC=CC=2)(O)[C@H](C2C=CC=CC=2)O)C=CC=CC=1>C1(OC)C=CC=CC=1>[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

Participants

4

Reactant 2

HCID 7000031(2S)-1,1,2-Triphenyl-1,2-ethanediolHCID 178488147HCID 178488147, compound

Product 1

HCID 9568614Esomeprazole

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A suspension of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.09 mmol) in anisole (8.8 ml) at ambient temperature was stirred for 72 h. The solid was filtered, was washed with anisole (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (265 mg, 79%, 96.6% e.e.) as a white powder.

Workup

  1. filtrationThe solid was filtered
  2. washwas washed with anisole (2×2 ml)
  3. customwas dried in vacuo

Sources & evidence

ORD record
ord-58247da10e284862be06ecd8b404c090
Source dataset
uspto-grants-2010_09
Patent number
US07799925B2

Reaction notes

Loading…