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

HRID 1906602
Notes
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Reaction equation

HRID 1906602 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:15]/[OH:16])/[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:6]=1.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>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:15][O:16][CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[N:6]=1
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 t-butyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate are dispersed in 250 ml of dry acetonitrile. 13.7 g (50 mmol) of p-nitrobenzyl bromoacetate and 12.9 ml (75 mmol) of N-ethyldiisopropylamine are now added thereto at room temperature while stirring. 7.5 g (50 mmol) of sodium iodide are added thereto 5 minutes later. 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 solution obtained is washed four times with a total of 2 l of water. The aqueous phase 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 t-butyl 2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]-acetate of melting point 146.8° C. (decomposition).

Workup

  1. custom5 minutes
  2. stirringThe mixture is stirred at room temperature for 3.5 hours in an argon atmosphere
  3. customThe solvent is subsequently removed by evaporation
  4. additionthe residue is diluted with 500 ml of ethyl acetate
  5. customThe solution obtained
  6. washis washed four times with a total of 2 l of water
  7. extractionThe aqueous phase is extracted with 300 ml of ethyl acetate
  8. dry with materialthe combined ethyl acetate solutions are dried over sodium sulphate
  9. customevaporated to dryness
  10. customAfter crystallization from ethyl acetate/hexane, there

Sources & evidence

ORD record
ord-11b4202a64e841d6ae829c14e34d4748
Source dataset
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04652651

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes