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

HRID 1715710Notes

Reaction equation

HRID 1715710 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(#N)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 6342AcetonitrileSolvent

Procedure

A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of acetonitrile (4 ml) at reflux temperature. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with acetonitrile (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (239 mg, 71%, 95% e.e.) as an off-white powder.

Workup

  1. temperatureat reflux temperature
  2. dissolutionOn dissolution
  3. filtrationThe precipitate was filtered
  4. washwas washed with acetonitrile (2×2 ml)
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-93ec83702981486c97947033d8690db8
Source dataset
uspto-grants-2010_09
Patent number
US07799925B2

Reaction notes

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