Water → HCID 88737397, compound

HRID 1164568Notes

Reaction equation

HRID 1164568 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].C(=O)(O)[O-].[Na+].O.Br[CH2:12][C:13]([CH2:15][C:16]([NH:18][CH:19]1[C:39](=[O:40])[N:21]2[C:22]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[CH:23][CH2:24][S:25][C@H:20]12)=[O:17])=O>O1CCCC1>[NH2:1][C:2]1[S:3][CH:12]=[C:13]([CH2:15][C:16]([NH:18][CH:19]2[C:39](=[O:40])[N:21]3[C:22]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=4)=[O:27])=[CH:23][CH2:24][S:25][C@H:20]23)=[O:17])[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 886077454-Nitrobenzyl 7-[2-(2-bromoacetyl)acetamido]-3-cephem-4-carboxylate

Product 1

HCID 88737397HCID 88737397, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiourea (1.13 g), sodium bicarbonate (1.24 g) and water (20 ml) were added to a solution of 4-nitrobenzyl 7-[2-(2-bromoacetyl)acetamido]-3-cephem-4-carboxylate (6.15 g) in tetrahydrofuran (60 ml), and stirred at room temperature for an hour. After concentrating the resultant solution under reduced pressure, the residue was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The oily residue was subjected to column chromatography on silica gel, and eluted with benzene, a mixture of benzene (1 part) and ethyl acetate (1 part) and then ethyl acetate in turn. The ethyl acetate fractions were collected and concentrated under reduced pressure to give 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)acetamido]-3-cephem-4-carboxylate (1.5 g).

Workup

  1. concentrationAfter concentrating the resultant solution under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with benzene
  7. additiona mixture of benzene (1 part) and ethyl acetate (1 part)
  8. customThe ethyl acetate fractions were collected
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f1d94e7058c45bcb04c33c9edb9d1c1
Source dataset
uspto-grants-1983_01
Patent number
US04370326

Reaction notes

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