Water → HCID 178462809, compound

HRID 1884909Notes

Reaction equation

HRID 1884909 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[N:19]=[C:18]([NH:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]3)[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[CH2:28][CH3:29])[CH:5]=1.O.[Li+].[OH-]>CO>[CH2:28]([N:15]1[CH:14]=[N:13][C:12]2[C:16]1=[N:17][C:18]([NH:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]1)=[N:19][C:11]=2[NH:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:30])=[O:2])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178462810HCID 178462810, compound

Product 1

HCID 178462809HCID 178462809, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.8 g (38.5 mmol) of 3-[9-ethyl-2-(trans-4-hydroxy-cyclohexylamino)-9H-purin-6-yl-amino]-benzoic acid methyl ester is suspended in 400 ml of MeOH, 77 ml of H2O and 77 ml of LiOH solution (1M), and stirred for 75 min at 80° C. After completion, the MeOH is removed under reduced pressure and the aqueous layer is washed with EtOAc (2 fold). The aqueous layer is then slowly treated with 1N HCl solution to pH 4-4.5. The precipitate is filtered off and washed to neutral pH to obtain 13.2 g (87% yield) of 3-[9-ethyl-2-(trans-4-hydroxy-cyclohexylamino)-9H-purin-6-yl-amino]-benzoic acid; Rf=0.34; (CH3Cl/MeOH/H2O/CH3COOH 85/13/1.5/0.5); m.p. 317° C.; ESI-MS: 397 (M+H)+.

Workup

  1. customAfter completion, the MeOH is removed under reduced pressure
  2. washthe aqueous layer is washed with EtOAc (2 fold)
  3. additionThe aqueous layer is then slowly treated with 1N HCl solution to pH 4-4.5
  4. filtrationThe precipitate is filtered off
  5. washwashed to neutral pH

Sources & evidence

ORD record
ord-0bbac57976644fd89b9b8e03de4bab57
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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