Sodium Chloride → HCID 131712941, compound

HRID 1164427Notes

Reaction equation

HRID 1164427 reaction equation
[C:1]([O:5][C:6]([NH:8]/[N:9]=[C:10]1/[C@H:11]2[S:16][CH2:15][C:14]([CH3:17])=[C:13]([C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19])[N:12]2[C:26]/1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][NH:9][C@@H:10]1[C:26](=[O:27])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]([Cl:23])([Cl:24])[Cl:25])=[O:19])=[C:14]([CH3:17])[CH2:15][S:16][C@H:11]12)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 140338070HCID 140338070, compound

Product 1

HCID 131712941HCID 131712941, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In tetrahydrofuran (20 ml) is dissolved 2,2,2-trichloroethyl (E)-7-t-butoxycarbonylhydrazono-3-methyl-3-cephem-4-carboxylate (4.60 g), and under ice-cooling, a 1 M tetrahydrofuran solution of borane-tetrahydrofuran complex (23 ml) is added dropwise. The mixture is stirred at that temperature for 30 minutes. The reaction mixture is poured in a mixture of ethyl acetate (150 ml) and aqueous sodium chloride (200 ml). The organic layer is taken, dried over magnesium sulfate and concentrated. The residual oil is subjected to silica gel (50 g) column chromatography and elution is carried out with ethyl acetate-benzene. The above procedure gives crystals of 2,2,2-trichloroethyl 7β-t-butoxycarbonylhydrazino-3-methyl-3-cephem-4-carboxylate (2.49 g).

Workup

  1. temperatureunder ice-cooling
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. washThe residual oil is subjected to silica gel (50 g) column chromatography and elution

Sources & evidence

ORD record
ord-0e31274a0c71416ebc1038af4996cc15
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

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