Tetrahydrofuran → Benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetate

HRID 358079Notes

Reaction equation

HRID 358079 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:15]1[N:19]=[C:18]([NH2:20])[S:17][N:16]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[C:26]1([C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N+]=[N-])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(OCC)(=O)C>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:15]1[N:19]=[C:18]([NH2:20])[S:17][N:16]=1)[C:12]([O:14][CH:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 545194092-Tert-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid

Product 1

HCID 54536722Benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 2-tert-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid (syn isomer (20 g) in ethyl acetate (200 ml) and tetrahydrofuran (100 ml) was added dropwise a solution of diphenyldiazomethane in ethyl acetate (0.9 m mole/ml, 80 ml) at ambient temperature, and the mixture was stirred for an hour. The reaction mixture was washed with a saturated aqueous sodium bicarbonate and an aqueous sodium chloride, and then dried over magnesium sulfate. The solution was evaporated to give benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetate (syn isomer) (15.0 g), mp 164° C. (dec.).

Workup

  1. washThe reaction mixture was washed with a saturated aqueous sodium bicarbonate
  2. dry with materialan aqueous sodium chloride, and then dried over magnesium sulfate
  3. customThe solution was evaporated

Sources & evidence

ORD record
ord-0f32617ef6924e659f20df6129abfa0c
Source dataset
uspto-grants-1984_08
Patent number
US04464369

Reaction notes

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