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

HRID 1715713Notes

Reaction equation

HRID 1715713 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>C(O)C>[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 702EthanolSolvent

Procedure

A suspension of omeprazole (20 g, 57.9 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (25.2 g, 86.9 mmol) in ethanol (700 ml) at ambient temperature was stirred for 30 h. The solid was filtered, was washed with ethanol (2×150 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (24.1 g, 90%, 95.5% e.e.) as a white powder.

Workup

  1. filtrationThe solid was filtered
  2. washwas washed with ethanol (2×150 ml)
  3. customwas dried in vacuo

Sources & evidence

ORD record
ord-19d24783bfca415b87d190311e424933
Source dataset
uspto-grants-2010_09
Patent number
US07799925B2

Reaction notes

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