Water → Benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetate

HRID 358080Notes

Reaction equation

HRID 358080 reaction equation
N(OC(C)(C)C)=O.[C:8]([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:35]1[N:39]=[C:38](N)[S:37][N:36]=1)[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(OCC)(=O)C.O>O1CCCC1>[C:8]([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:35]1[N:39]=[CH:38][S:37][N:36]=1)[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10906Tert-Butyl nitriteHCID 54536722Benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetate

Product 1

HCID 54175448Benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetateYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of t-butyl nitrite (3.2 g) in tetrahydrofuran (20 ml) was added dropwise to a solution of benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetate (syn isomer) (10 g) in tetrahydrofuran (100 ml) at 50° to 53° C. under stirring, and the mixture was stirred at the same temperature for 25 minutes. The reaction mixture was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with an aqueous sodium chloride and dried over magnesium sulfate. The solution was evaporated and the residue was subjected to column chromatography on silica gel. The elution was carried out with a mixture of benzene and ethyl acetate (19:1) and the eluates containing the object compound were evaporated to give benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetate (syn isomer) (7.1 g), mp. 139° to 141° C.

Workup

  1. stirringthe mixture was stirred at the same temperature for 25 minutes
  2. washThe separated organic layer was washed with an aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customThe solution was evaporated
  5. washThe elution
  6. additionwas carried out with a mixture of benzene and ethyl acetate (19:1)
  7. additionthe eluates containing the object compound
  8. customwere evaporated

Sources & evidence

ORD record
ord-5b453297b9f34280aa978a651c9e7877
Source dataset
uspto-grants-1984_08
Patent number
US04464369

Reaction notes

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