Methanol → 1-((1R,2R)-2-Methyl-cyclohexyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid

HRID 1750233Notes

Reaction equation

HRID 1750233 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[CH3:17])=[C:6]([NH:18][C:19](=O)[CH2:20][C:21]2[S:25][CH:24]=[N:23][CH:22]=2)[CH:5]=1.CO.[OH-].[Na+]>C1COCC1>[CH3:17][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[N:10]1[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:27])=[CH:5][C:6]=2[N:18]=[C:19]1[CH2:20][C:21]1[S:25][CH:24]=[N:23][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 867144394-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester

Product 1

HCID 867144411-((1R,2R)-2-Methyl-cyclohexyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.35 g 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester was dissolved in 6 ml of THF and 3 ml of methanol and 7 ml of 2 M aqueous sodium hydroxide solution were added at rt for 4 h. The reaction was concentrated and the pH was adjusted to 5 by addition of 2 M aqueous hydrochloric acid, and the mixture was extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulphate and concentrated to afford 0.32 g (95%) of 1-((1R,2R)-2-Methyl-cyclohexyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe pH was adjusted to 5 by addition of 2 M aqueous hydrochloric acid
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd3df0e5be9b4ca2bfa36f98cd22cc35
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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