Ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate → (1R,3S)-5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 553569Notes

Reaction equation

HRID 553569 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[N:12]([CH2:20][CH2:21][O:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH:25]([O:29][CH2:30][C:31]4[N:32]=[C:33]([C:37]5[CH:38]=[C:39]([CH3:43])[CH:40]=[CH:41][CH:42]=5)[O:34][C:35]=4[CH3:36])[CH2:24]3)[C:9]2=[CH:10][N:11]=1>C1COCC1.CO.[OH-].[Li+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[N:12]([CH2:20][CH2:21][O:22][C@@H:23]3[CH2:28][CH2:27][CH2:26][C@H:25]([O:29][CH2:30][C:31]4[N:32]=[C:33]([C:37]5[CH:38]=[C:39]([CH3:43])[CH:40]=[CH:41][CH:42]=5)[O:34][C:35]=4[CH3:36])[CH2:24]3)[C:9]2=[CH:10][N:11]=1

Participants

4

Reactant 1

HCID 67463595Ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 59820059(1R,3S)-5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

60 mg of ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate are dissolved in 2 ml of THF/methanol 3:1, and 0.15 ml of a 1 N lithium hydroxide solution is added. The mixture is stirred at room temperature for 24 h. All volatile components are removed under reduced pressure, the residue is taken up in DMF/acetonitrile, 70 μl of TFA are added and the mixture is filtered and purified by RP-HPLC. This gives 14 mg of (1R,3S)-5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid as a colorless oil. C31H37N3O7 (563.66), MS (ESI): 564 (M+H+).

Workup

  1. additionis added
  2. customAll volatile components are removed under reduced pressure
  3. addition70 μl of TFA are added
  4. filtrationthe mixture is filtered
  5. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-8bb3eb04a3054825b5162dc31b492dd6
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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