Sodium Hydroxide → HCID 25027863, compound

HRID 238887Notes

Reaction equation

HRID 238887 reaction equation
C[O:2][C:3](=[O:33])[C:4]([CH3:32])([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)=[O:8])[CH3:5].[OH-].[Na+]>O1CCCC1.CO>[CH3:32][C:4]([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]=1[O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]([F:29])([F:31])[F:30])=[CH:25][CH:26]=1)=[O:8])([CH3:5])[C:3]([OH:33])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68842026HCID 68842026, compound

Product 1

HCID 25027863HCID 25027863, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.13 g 2-methyl-2-{[1-(4-trifluoromethoxy-benzyloxy)-5,6,7,8-tetrahydro-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester was dissolved in 5 ml of tetrahydrofuran and 0.5 ml of methanol. To this was added 0.42 ml of 2 M NaOH (aq), and the reaction was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, diluted with 5 ml of ethyl acetate and 5 ml of water and acidified to pH 3 with 1N HCl (aq). The organic layer was separated, dried over magnesium sulphate and concentrated in vacuo to give 99 mg of 2-methyl-2-{[1-(4-trifluoromethoxy-benzyloxy)-5,6,7,8-tetrahydro-naphthalene-2-carbonyl]-amino}-propionic acid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with 5 ml of ethyl acetate and 5 ml of water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-953ac73933ee4b708b71d2fe446710aa
Source dataset
uspto-grants-2014_02
Patent number
US08642643B2

Reaction notes

Loading…