Water → benzhydryl 2-[4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-(hydroxymethyl)-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylate

HRID 330707Notes

Reaction equation

HRID 330707 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:45]/[O:46][CH3:47])/[C:12]([NH:14][C:15]2([CH2:43][OH:44])[CH2:19][O:18][N:17]([C:20]3([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH2:24][CH2:23][C:22](=[O:25])[O:21]3)[C:16]2=[O:42])=[O:13])[N:10]=1)=O.CNC(=S)[S-].[Na+].O>CN(C)C=O>[NH2:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:45]/[O:46][CH3:47])/[C:12]([NH:14][C:15]2([CH2:43][OH:44])[CH2:19][O:18][N:17]([C:20]3([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH2:24][CH2:23][C:22](=[O:25])[O:21]3)[C:16]2=[O:42])=[O:13])[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5366415Metam-sodiumHCID 88594920benzhydryl 2-[4-[[(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-(hydroxymethyl)-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylate

Product 1

HCID 88594853benzhydryl 2-[4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-(hydroxymethyl)-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylateYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 3 ml of dimethylformamide was dissolved 170 mg of the Compound (9a) obtained as above. To the solution was added, under ice-cooling, 48 mg of sodium N-methyldithiocarbamate, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The concentrate was subjected to a silica-gel column chromatography, eluting with ethyl acetate - n-hexane (2:1) to give 115 mg of the above-titled Compound (9b).

Workup

  1. customobtained as above
  2. additionTo the solution was added, under ice-
  3. temperaturecooling
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with ethyl acetate - n-hexane (2:1)

Sources & evidence

ORD record
ord-10d2685e73e940e0b388a0834851b0d8
Source dataset
uspto-grants-1990_01
Patent number
US04897489

Reaction notes

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