Triethylamine → 2,2,2-Trichloroethyl 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylate

HRID 1660598Notes

Reaction equation

HRID 1660598 reaction equation
Cl.[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH2:19])[C@H:5]2[S:4]1.C(N(CC)CC)C.[C:28]1([CH2:34][C:35](Cl)=[S:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:14])[Cl:15])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH:19][C:35](=[S:36])[CH2:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:5]2[S:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochlorideHCID 19906501Benzylthiocarbonyl chloride

Product 1

HCID 1317112522,2,2-Trichloroethyl 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylateYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

2,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (3.0 g) was suspended in dried dichloromethane (50 ml) and then dissolved by adding triethylamine (0.72 g) and dimethylamiline (1.9 g) under cooling at -15° C. To a mixture was dropwise added a solution of phenylthioacetyl chloride (2.2 g) in dried dichloromethane (10 ml) under stirring, and the mixture was stirred for 1.5 hours at the same temperature. After the reaction, the reaction mixture was in turn washed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water and then dried. After the solvent was distilled off, ether was added to the residue, after which the precipitated crystals were collected by filtration are dried to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylate (3.4 g), mp 140° to 142° C.

Workup

  1. dissolutiondissolved
  2. stirringthe mixture was stirred for 1.5 hours at the same temperature
  3. customAfter the reaction
  4. washwashed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water
  5. customdried
  6. distillationAfter the solvent was distilled off
  7. additionether was added to the residue
  8. filtrationafter which the precipitated crystals were collected by filtration
  9. customare dried

Sources & evidence

ORD record
ord-3a6a2932e1cf44c5bbf74644164240a8
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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