Acetyl bromide → HCID 67712651, compound

HRID 1200114Notes

Reaction equation

HRID 1200114 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O:24][CH:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])=[C:15]([CH2:19][S:20][CH3:21])[CH2:16][S:17](=O)[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(=CC)C.C(Br)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O:24][CH:25]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[O:23])=[C:15]([CH2:19][S:20][CH3:21])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 10482Acetyl bromideHCID 105532-Methyl-2-buteneHCID 516892Sodium BicarbonateHCID 67712516HCID 67712516, compound

Product 1

HCID 67712651HCID 67712651, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7-(2-phenylacetamido)-3-methylthiomethyl-3-cephem-4-carboxylate-1-oxide (15.1 g) in methylene chloride (150 ml) was added 2-methyl-2-butene (5.7 ml), followed by adding dropwise acetyl bromide (5.2 ml) under ice-cooling and stirring for half an hour. After addition of water, the mixture was adjusted to pH about 5 with an aqueous solution of sodium bicarbonate, washed three times with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then evaporated under reduced pressure to give benzhydryl 7-[2-phenylacetamido)-3-methylthiomethyl-3-cephem-4-carboxylate (13.5 g).

Workup

  1. temperaturecooling
  2. washwashed three times with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a68f029adf534d61b18f760648911cec
Source dataset
uspto-grants-1990_02
Patent number
US04904652

Reaction notes

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