Hydrochloric Acid → 2,2,2-Trichloroethyl 2-methyl-7-[2-(1,3,4-thiadiazol-2-yithio)acetamido]-3-cephem-4-carboxylate

HRID 1764010Notes

Reaction equation

HRID 1764010 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.CN(C)C1C=CC=CC=1.[S:30]1[CH:34]=[N:33][N:32]=[C:31]1[S:35][CH2:36][C:37](O)=[O:38].C1(N=C=NC2CCCCC2)CCCCC1.Cl>ClCCl.C(N(CC)CC)C>[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:37](=[O:38])[CH2:36][S:35][C:31]3[S:30][CH:34]=[N:33][N:32]=3)[C@H:5]2[S:4]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 10868DicyclohexylcarbodiimideHCID 126346932-(1,3,4-Thiadiazol-2-ylsulfanyl)acetic acidHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 128340152,2,2-Trichloroethyl 2-methyl-7-[2-(1,3,4-thiadiazol-2-yithio)acetamido]-3-cephem-4-carboxylateYield 89.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (3.82 g) was suspended in dried dichloromethane (80 ml) and dissolved by adding under stirring and ice-cooling a solution of triethylamine (0.9 g) and dimethylaniline (0.15 g) in dichloromethane (20 ml). To the solution were added (1,3,4-thiadiazol-2-ylthio)acetic acid (1.8 g) and dicyclohexylcarbodiimide (2.25 g) under stirring and ice-cooling, and the mixture was stirred for 1 hour under ice-cooling. To the reaction mixture, was added 5% hydrochloric acid (50 ml), and the mixture was stirred for 30 minutes, after which the organic layer was separated, washed in turn with 5% hydrochloric acid, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and then dried over magnesium sulfate. The solvent was distilled off to give pale brown powder of 2,2,2-trichloroethyl 2-methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)acetamido]-3-cephem-4-carboxylate (4.5 g), mp 130° to 140° C. (dec.).

Workup

  1. dissolutiondissolved
  2. additionby adding
  3. stirringunder stirring
  4. temperatureice-cooling
  5. stirringthe mixture was stirred for 1 hour under ice-
  6. temperaturecooling
  7. stirringthe mixture was stirred for 30 minutes
  8. customafter which the organic layer was separated
  9. washwashed in turn with 5% hydrochloric acid
  10. dry with materiala saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and then dried over magnesium sulfate
  11. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-32a336d9129f42f3a41df1379480dff8
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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