Hydrochloric Acid → 1-{[1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carbonyl]-amino}-cycloheptanecarboxylic acid

HRID 1750164Notes

Reaction equation

HRID 1750164 reaction equation
C[O:2][C:3]([C:5]1([NH:12][C:13]([C:15]2[CH:34]=[CH:33][C:18]3[N:19]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:20]([CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[N:21][C:17]=3[CH:16]=2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C1COCC1.[OH-].[Na+].Cl>C(O)C>[CH2:29]([CH:28]([N:19]1[C:18]2[CH:33]=[CH:34][C:15]([C:13]([NH:12][C:5]3([C:3]([OH:4])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)=[O:14])=[CH:16][C:17]=2[N:21]=[C:20]1[CH2:22][C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH2:31][CH3:32])[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 867143721-{[1-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzimidazole-5-carbonyl]-amino}-cycloheptanecarboxylic acid methyl ester

Product 1

HCID 734420311-{[1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carbonyl]-amino}-cycloheptanecarboxylic acidYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

400 mg of 1-{[1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carbonyl]-amino}-cycloheptanecarboxylic acid methyl ester were dissolved in 4 ml ethanol and 2 ml THF and 4 ml of 2 M aqueous sodium hydroxide solution were added. After stirring at room temperature over night, the reaction mixture was brought to pH 3 by addition of 2 M aqueous hydrochloric acid and extracted with ethyl acetate three times. The combined organic phases were dried over magnesium sulphate and concentrated to yield 100 mg (26%) of 1-{[1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carbonyl]-amino}-cycloheptanecarboxylic acid.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b34c61a3f06644c6a75018bd31dd707b
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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