Esomeprazole → HCID 178488151, compound

HRID 227278

Reaction equation

HRID 227278 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S@@:12]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)=[O:13])=[N:4][CH:3]=1.[CH:25]1([C@H:31]([NH2:33])[CH3:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(#N)C>[CH:25]1([C@H:31]([NH3+:33])[CH3:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:16]2[NH:15][C:14]([S@:12]([CH2:11][C:5]3[C:6]([CH3:10])=[C:7]([O:8][CH3:9])[C:2]([CH3:1])=[CH:3][N:4]=3)=[O:13])=[N:18][C:17]=2[CH:19]=1

Participants

4

Reactant 2

HCID 9568614EsomeprazoleHCID 10997046(1R)-1-Cyclohexylethanamine

Product 1

HCID 178488151HCID 178488151, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-omeprazole (1.0 g, 2.9 mmol) was dissolved in acetonitrile (10 ml). (R)-1-cyclohexyl ethyl amine (0.83 ml, 5.7 mmol) was added to the solution whereupon a white solid precipitated. After 45 minutes acetonitril (10 ml) was added to the thick reaction mass and stirring was continued for 45 minutes. The precipitate was filtered off, washed with acetonitrile, and dried. 0.5 g of the title compound was obtained.

Workup

  1. customprecipitated
  2. additionAfter 45 minutes acetonitril (10 ml) was added to the thick reaction mass
  3. filtrationThe precipitate was filtered off
  4. washwashed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-ef8b32b7427c427c9f0cb2876b38390a
Source dataset
uspto-grants-2009_07
Patent number
US07560472B2

Linked notes

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