Sodium Hydroxide → HCID 54452492, compound

HRID 1262757Notes

Reaction equation

HRID 1262757 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=O)[C:12]([OH:14])=[O:13].[C:16]([O:20][C:21]([CH2:23][O:24][NH2:25])=[O:22])([CH3:19])([CH3:18])[CH3:17].[OH-].[Na+]>O.N1C=CC=CC=1.O1CCCC1>[C:16]([O:20][C:21]([CH2:23][O:24][N:25]=[C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]([OH:14])=[O:13])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 9834233HCID 9834233, compoundHCID 12919121tert-Butyl (aminooxy)acetate

Product 1

HCID 54452492HCID 54452492, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-naphthylglyoxylic acid (6 g) in water (60 ml) and pyridine (6 ml) was added tert-butoxycarbonylmethoxyamine (9 g) in tetrahydrofuran (40 l) at room temperature and the mixture was stirred at the same temperature for 3 hours. The resultant mixture was adjusted to pH 7.5 with 10% aqueous sodium hydroxide and washed with ethyl acetate. The aqueous layer was acidified to pH 2.0 with 10% hydrochloric acid and the acidified solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solution was evaporated in vacuo to give 2-(tert-butoxycarbonylmethoxyimino)-2-(2-naphthyl)acetic acid (syn isomer) (8 g).

Workup

  1. washwashed with ethyl acetate
  2. extractionthe acidified solution was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-bfbeddf8aca04300affdbe39be554700
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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