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

HRID 2290491
Notes
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Reaction equation

HRID 2290491 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 atmosphere. 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-7c4dad3d1cd443dcb33e5eb4d52bd3e7
Source dataset
uspto-grants-1986_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04617150

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes