Triethylamine → HCID 68141821, compound

HRID 1729675Notes

Reaction equation

HRID 1729675 reaction equation
[NH2:1][C@@H:2]1[C:27](=[O:28])[N:4]2[C@@H:5]([C:11]([O:13][CH:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[C@@:6]([Cl:10])([CH3:9])[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[O:36]([CH2:43][C:44](Cl)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[Cl:10][C@@:6]1([CH3:9])[C@H:5]([C:11]([O:13][CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:12])[N:4]2[C:27](=[O:28])[C@@H:2]([NH:1][C:44](=[O:45])[CH2:43][O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:3]2[S:8][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 68140931HCID 68140931, compound

Product 1

HCID 68141821HCID 68141821, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzhydryl 7β-amino-3β-chloro-3α-methylcepham-4α-carboxylate (209 mg) in methylene chloride (3 ml) is added triethylamine (56 mg), and the mixture is mixed with a solution of phenoxyacetyl chloride (79 mg) in methylene chloride (2 ml) under ice cooling. After being left to stand for 2 hours, the mixture is washed successively with dilute hydrochloric acid, 5% aqueous sodium hydrogen carbonate, and water, then dried, and evaporated in vacuo. Recrystallization of the residue with a mixture of ether and petroleum ether gives benzhydryl 3β-chloro-3α-methyl-7β-phenoxyacetamidocepham-4α-carboxylate (220 mg). Yield: 82%.

Workup

  1. waitAfter being left
  2. washthe mixture is washed successively with dilute hydrochloric acid, 5% aqueous sodium hydrogen carbonate, and water
  3. customdried
  4. customevaporated in vacuo
  5. customRecrystallization of the residue
  6. additionwith a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-bc7c3ecc0870480385d5df242e8ed474
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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