ethyl 4-[(6-chloro-5-[4'-(tetrahydrofuran-3-ylcarbamoyl)biphenyl-4-yl]-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]cyclohexanecarboxylate → 4-({6-chloro-5-[4'-(tetrahydrofuran-3-ylcarbamoyl)biphenyl-4-yl]-1H-benzimidazol-2-yl}oxy)cyclohexanecarboxylic acid

HRID 340784Notes

Reaction equation

HRID 340784 reaction equation
[Cl:1][C:2]1[C:3]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][C:40]([C:43](=[O:50])[NH:44][CH:45]4[CH2:49][CH2:48][O:47][CH2:46]4)=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH:11]3[CH2:16][CH2:15][CH:14]([C:17]([O:19]CC)=[O:18])[CH2:13][CH2:12]3)[N:7](COCC[Si](C)(C)C)[C:6]=2[CH:30]=1.O([Si](C)(C)C)[K]>C1COCC1>[Cl:1][C:2]1[C:3]([C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:42]=[CH:41][C:40]([C:43](=[O:50])[NH:44][CH:45]4[CH2:49][CH2:48][O:47][CH2:46]4)=[CH:39][CH:38]=3)=[CH:35][CH:36]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH:11]3[CH2:12][CH2:13][CH:14]([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]3)[NH:7][C:6]=2[CH:30]=1

Participants

4

Reactant 2

HCID 71073802ethyl 4-[(6-chloro-5-[4'-(tetrahydrofuran-3-ylcarbamoyl)biphenyl-4-yl]-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]cyclohexanecarboxylateHCID 178504318HCID 178504318, compound

Product 1

HCID 682405134-({6-chloro-5-[4'-(tetrahydrofuran-3-ylcarbamoyl)biphenyl-4-yl]-1H-benzimidazol-2-yl}oxy)cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[(6-chloro-5-[4′-(tetrahydrofuran-3-ylcarbamoyl)biphenyl-4-yl]-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]cyclohexanecarboxylate (0.115 g, 0.160 mmol) in THF (3 mL) was added KOTMS (0.062 g, 0.483 mmol). The reaction was maintained overnight at ambient temperature. Then the volatiles were removed in vacuo, and the resulting residue was acidified with 1 N aqueous HCl, and extracted with EtOAc. The organic phase was concentrated to afford the desired carboxylic acid intermediate, which was used in the next step without further purification.

Workup

  1. customThen the volatiles were removed in vacuo
  2. extractionextracted with EtOAc
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-fd79e636e5f74feea23d2706cb2452a6
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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