Sodium Iodide → t-Butyl 2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]-acetate

HRID 482839Notes

Reaction equation

HRID 482839 reaction equation
[C:1]([O:5][C:6](=[O:16])/[C:7](/[C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)=[N:8]\[OH:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20].C(N(C(C)C)C(C)C)C.[I-].[Na+]>C(#N)C>[C:1]([O:5][C:6](=[O:16])[C:7]([C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)=[N:8][O:9][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 70153214-Nitrobenzyl bromoacetateHCID 13826576tert-butyl 2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetate

Product 1

HCID 53971680t-Butyl 2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]-acetateYield 75.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.1 g (25 mmol) of 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetic acid t-butyl ester are dispersed in 250 ml of dry acetonitrile. There are now added thereto at room temperature while stirring 13.7 g (50 mmol) of 4-nitrobenzyl bromoacetate and 12.9 ml (75 mmol) of N-ethyldiisopropylamine. 5 minutes later 7.5 g (50 mmol) of sodium iodide are added thereto. The mixture is stirred at room temperature for 3.5 hours in an argon temperature. The solvent is subsequently removed by evaporation and the residue is diluted with 500 ml of ethyl acetate. The resulting solution is washed four times with a total of 2 l of water. The water is extracted with 300 ml of ethyl acetate and the combined ethyl acetate solutions are dried over sodium sulphate and evaporated to dryness. After crystallization from ethyl acetate/hexane, there are obtained 8.2 g (75%) of 2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]-acetic acid t-butyl ester of melting point 146.8° (decomposition).

Workup

  1. additionThere are now added
  2. customThe solvent is subsequently removed by evaporation
  3. additionthe residue is diluted with 500 ml of ethyl acetate
  4. washThe resulting solution is washed four times with a total of 2 l of water
  5. extractionThe water is extracted with 300 ml of ethyl acetate
  6. dry with materialthe combined ethyl acetate solutions are dried over sodium sulphate
  7. customevaporated to dryness
  8. customAfter crystallization from ethyl acetate/hexane, there

Sources & evidence

ORD record
ord-d8ba1a3368094d49a2e664a68b0d391c
Source dataset
uspto-grants-1986_03
Patent number
US04576751

Reaction notes

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