Water → HCID 56636309, compound

HRID 981901Notes

Reaction equation

HRID 981901 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, 1N 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-7-phenylacetamido-cepham-4-carboxylate.

Workup

  1. filtrationAfter filtration
  2. customthe diluted reaction mixture
  3. washwas subsequently washed with water, 1N 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-40714d865e2843989f7f9beaca1f0bf8
Source dataset
uspto-grants-1991_02
Patent number
US04994454

Reaction notes

Loading…