Iodoacetamide → HCID 131715884, compound

HRID 1194160Notes

Reaction equation

HRID 1194160 reaction equation
[C:1]([NH:20][C@@H:21]1[C:59](=[O:60])[N:23]2[C:24]([C:43]([O:45][CH:46]([C:53]3[CH:58]=CC=C[CH:54]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=O)=[C:25](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[CH2:26][S:27][C@H:22]12)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH-:61].[Na+].I[CH2:64][C:65]([NH2:67])=[O:66].C(OCC)(=O)C.[CH:74](N(C(C)C)CC)([CH3:76])[CH3:75]>CN(C)C=O>[C:1]([NH:20][C@@H:21]1[C:59](=[O:60])[N:23]2[C:24]([C:43]([O:45][CH:46]([C:53]3[CH:58]=[CH:76][CH:74]=[CH:75][CH:54]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[S:61])=[C:25]([CH2:64][C:65](=[O:66])[NH2:67])[CH2:26][S:27][C@H:22]12)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 3727IodoacetamideHCID 8857Ethyl AcetateHCID 28015Sodium hydrosulfideHCID 81531DiisopropylethylamineHCID 70378209HCID 70378209, compound

Product 1

HCID 131715884HCID 131715884, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cooled (-25° C.) solution of 1.47 g (1.72 mM) of benzhydryl 7β-tritylamino-3-diphenylphosphoryloxy-3-cephem-4-carboxylate in 15 ml of N,N-dimethylformamide were added a solution of 0.15 g (1.89 mM) of 70% sodium hydrosulfide in 5 ml of N,N-dimethylformamide and 0.33 g (2.58 mM) of diisopropylethylamine. The mixture was stirred at -20° to -15° C. for one hour, and 0.64 g (3.44 mM) of iodoacetamide was added at the same temperature, and the mixture was stirred for one hour. After the reaction, ethyl acetate (100 ml) was added, and the mixture was washed with 0.5% hydrochloric acid (50 ml) and a saturated aqueous sodium chloride solution (50 ml×2), successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent; benzene: ethyl acetate=1:1) to give 0.56 g of benzhydryl 7β -tritylamino-3-carbamoylmethylthio-3-cephem-4-carboxylate.

Workup

  1. stirringthe mixture was stirred for one hour
  2. additionwas added
  3. washthe mixture was washed with 0.5% hydrochloric acid (50 ml)
  4. dry with materiala saturated aqueous sodium chloride solution (50 ml×2), successively, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (eluent; benzene: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5b7cf7e2859840e9b2d1d5bcb76eec1f
Source dataset
uspto-grants-1989_03
Patent number
US04812562

Reaction notes

Loading…