Acetyl bromide → HCID 67712651, compound

HRID 647566Notes

Reaction equation

HRID 647566 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-4d406f1e1a484ea28ad111cc6ae7a1b0
Source dataset
uspto-grants-1983_10
Patent number
US04409215

Reaction notes

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