Water → Dexlansoprazole Sesquihydrate

HRID 218450Notes

Reaction equation

HRID 218450 reaction equation
[CH3:1][C:2]1[C:3]([CH2:11][S@:12]([C:14]2[NH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[O:13])=[N:4][CH:5]=[CH:6][C:7]=1[N+]([O-])=[O:9].[OH-:23].[K+].O.C1(C)C=CC=CC=1.[F:33][C:34]([F:38])([F:37])[CH2:35][OH:36]>>[CH3:1][C:2]1[C:3]([CH2:11][S@:12]([C:14]2[NH:15][C:16]3[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:18]=2)=[O:13])=[N:4][CH:5]=[CH:6][C:7]=1[O:36][CH2:35][C:34]([F:38])([F:37])[F:33].[CH3:1][C:2]1[C:3]([CH2:11][S@:12]([C:14]2[NH:15][C:16]3[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:18]=2)=[O:13])=[N:4][CH:5]=[CH:6][C:7]=1[O:36][CH2:35][C:34]([F:38])([F:37])[F:33].[OH2:9].[OH2:23].[OH2:9]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 64092,2,2-TrifluoroethanolHCID 14797Potassium HydroxideHCID 469475292-((R)-((3-Methyl-4-nitro-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole

Product 1

HCID 71587692Dexlansoprazole SesquihydrateYield 90%

Conditions

Temperature
25 °C

Procedure

A solution of compound (II) (1.42 Kg) in 2,2,2-trifluoroethanol (6.40 L) is treated with potassium hydroxide (1.31 Kg). The reaction mixture is left to react at 90° C. for 1.5 hours and then cooled to 25° C. Water and toluene are added to the reaction mixture and the two newly formed phases are separated. Pure crystalline Dexlansoprazole sesquihydrate (1.56 Kg, 90% yield) can be isolated from the organic phase following the procedure reported in Example 2.

Workup

  1. waitThe reaction mixture is left
  2. customto react at 90° C. for 1.5 hours
  3. customthe two newly formed phases are separated

Sources & evidence

ORD record
ord-efd6a9e2354b4d0f831645bed8f05878
Source dataset
uspto-grants-2012_06
Patent number
US08198455B2

Reaction notes

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