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

HRID 1715707Notes

Reaction equation

HRID 1715707 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)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 3776IsopropanolSolvent

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 isopropyl alcohol (10 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 isopropyl alcohol (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (240 mg, 72%, 97% e.e.) as an off-white powder.

Workup

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

Sources & evidence

ORD record
ord-e01befcf7085433498b5854f8425edd5
Source dataset
uspto-grants-2010_09
Patent number
US07799925B2

Reaction notes

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