Hydrochloric Acid → HCID 12833997, compound

HRID 851588Notes

Reaction equation

HRID 851588 reaction equation
CN(C)C1C=CC=CC=1.Cl.[CH3:11][CH:12]1[CH:17]=[C:16]([C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19])[N:15]2[C:26](=[O:29])[CH:27]([NH2:28])[C@H:14]2[S:13]1.[C:30]([CH2:32][C:33](O)=[O:34])#[N:31].C1(N=C=NC2CCCCC2)CCCCC1.Cl>ClCCl.C(N(CC)CC)C>[CH3:11][CH:12]1[CH:17]=[C:16]([C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:23])[Cl:24])=[O:19])[N:15]2[C:26](=[O:29])[CH:27]([NH:28][C:33](=[O:34])[CH2:32][C:30]#[N:31])[C@H:14]2[S:13]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 12833997HCID 12833997, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of triethylamine (0.9 g) and dimethylaniline (0.15 g) in dichloromethane (20 ml) was added under stirring and ice-cooling to a suspension of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (3.82 g) in dried dichloromethane (80 ml). To the mixture were added cyanoacetic acid (0.85 g) and dicyclohexylcarbodiimide (2.25 g), and the mixture was stirred for 1 hour under ice-cooling. To the 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 colorless powder of 2,2,2-trichloroethyl 2-methyl-7-(2-cyanoacetamido)-3-cephem-4-carboxylate (3.5 g), mp 160° to 165° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-36b5ee90d94f49c09167b253344d8845
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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