Sodium Hydroxide → 2-Tert-butoxycarbonylmethoxyimino-2-(1,2,5-thiadiazol-3-yl)acetic acid

HRID 358082Notes

Reaction equation

HRID 358082 reaction equation
[S:1]1[N:5]=[CH:4][C:3]([C:6](=O)[C:7]([OH:9])=[O:8])=[N:2]1.[C:11]([O:15][C:16]([CH2:18][O:19][NH2:20])=[O:17])([CH3:14])([CH3:13])[CH3:12].[OH-].[Na+]>O1CCCC1.O>[C:11]([O:15][C:16]([CH2:18][O:19][N:20]=[C:6]([C:3]1[CH:4]=[N:5][S:1][N:2]=1)[C:7]([OH:9])=[O:8])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 12906559(1,2,5-Thiadiazol-3-yl)glyoxylic acidHCID 12919121tert-Butyl (aminooxy)acetate

Product 1

HCID 537432692-Tert-butoxycarbonylmethoxyimino-2-(1,2,5-thiadiazol-3-yl)acetic acidYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1,2,5-thiadiazol-3-yl)glyoxylic acid (6 g) in tetrahydrofuran (30 ml) and water (30 ml) was added tert-butoxycarbonylmethoxyamine (8.37 g) at ambient temperature. The mixture was adjusted to pH 4.5-5.0 with 4N aqueous sodium hydroxide and stirred at ambient temperature for 4 hours. The mixture was adjusted to pH 7.5 with 4N aqueous sodium hydroxide and washed with ethyl acetate (100 ml×2). The aqueous solution was acidified to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate (100 ml×2). The organic layer was washed with an aqueous sodium chloride and dried over magnesium sulfate. The solution was evaporated in vacuo to give 2-tert-butoxycarbonylmethoxyimino-2-(1,2,5-thiadiazol-3-yl)acetic acid (syn and anti mixture) (10.02 g).

Workup

  1. washwashed with ethyl acetate (100 ml×2)
  2. extractionextracted with ethyl acetate (100 ml×2)
  3. washThe organic layer was washed with an aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-df38488b7e454b3bb34fad0e4d1dffcb
Source dataset
uspto-grants-1984_08
Patent number
US04464369

Reaction notes

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