Methanol → HCID 58370210, compound

HRID 2062086Notes

Reaction equation

HRID 2062086 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([Cl:26])=[CH:18][C:17]=2[C:27](=[O:38])[NH:28][C:29]([C:33]([O:35]CC)=[O:34])([CH3:32])[CH2:30][CH3:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([Cl:26])=[CH:18][C:17]=2[C:27](=[O:38])[NH:28][C:29]([C:33]([OH:35])=[O:34])([CH3:32])[CH2:30][CH3:31])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66701209HCID 66701209, compound

Product 1

HCID 58370210HCID 58370210, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 41 mg of 4-[4-chloro-2-(1-ethoxycarbonyl-1-methyl-propylcarbamoyl)-naphthalen-1-yloxymethyl]-piperidine-1-carboxylic acid tert-butyl ester (see example 160, step a)) in 4 mL THF and 1 mL MeOH was treated with 4 mL of 2 M aqueous sodium hydroxide. The reaction mixture was stirred at room temperature overnight. The organic solvent was removed in vacuo. The residue was taken up in 6 ml of water and washed with ethyl acetate. It was treated with 2 M hydrochloric acid to adjust the pH to 5-6 and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate and concentrated to give 12 mg of 4-[2-(1-carboxy-1-methyl-propylcarbamoyl)-4-chloro-naphthalen-1-yloxymethyl]-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe organic solvent was removed in vacuo
  2. washwashed with ethyl acetate
  3. additionIt was treated with 2 M hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-802716c1fdd54cd0a23034cee39bb03f
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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