Water → HCID 56636309, compound

HRID 1031232Notes

Reaction equation

HRID 1031232 reaction equation
Br[CH2:2][C:3]1[CH2:4][S@:5](=[O:29])[C@@H:6]2[C@H:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16](=[O:28])[N:7]2[C:8]=1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].O.[Cl-].[NH4+].[Mg]>CN(C)C=O.C(OCC)(=O)C>[CH2:2]=[C:3]1[C@H:8]([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[N:7]2[C:16](=[O:28])[C@@H:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C@H:6]2[S@@:5](=[O:29])[CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 10917853HCID 10917853, compound

Product 1

HCID 56636309HCID 56636309, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 480 mg (1 mmole) of tert-butyl (1S,6R,7R)-3-bromomethyl-1-oxo-7-phenylacetamido-3-cephem-4-carboxylate in 12.5 ml of dimethylformamide was added 2.5 ml of water, 1 g of ammonium chloride and 500 mg of magnesium powder at 0° C. After stirring for 2 hours at 0° C. 100 ml of ethyl acetate was added. After filtration the diluted reaction mixture was subsequently washed with water, 1 N hydrochloric acid, brine, and dried with magnesium sulfate. After treating the dried solution with diethylether and n-hexane the title product was filtered off, washed with n-hexane and dried, yielding 382 mg of tert-butyl (1S,4R,6R,7R)-3-methylene-1-oxo-7phenylacetamido-cepham-4-carboxylate

Workup

  1. filtrationAfter filtration
  2. customthe diluted reaction mixture
  3. washwas subsequently washed with water, 1 N hydrochloric acid, brine
  4. dry with materialdried with magnesium sulfate
  5. additionAfter treating the dried solution with diethylether and n-hexane the title product
  6. filtrationwas filtered off
  7. washwashed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-a028c08aabdc4784bfa00ac6f2410489
Source dataset
uspto-grants-1992_04
Patent number
US05109132

Reaction notes

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