Triethylamine → HCID 70567479, compound

HRID 614643Notes

Reaction equation

HRID 614643 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](Cl)=[O:8].[NH2:10][CH:11]1[C:26](=[O:27])[N:13]2[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[CH2:16][S:17][C@H:12]12.C(N(CC)CC)C>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:10][CH:11]1[C:26](=[O:27])[N:13]2[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[CH2:16][S:17][C@H:12]12)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 127847593-Carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acid

Product 1

HCID 70567479HCID 70567479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 100 milligrams (0.6 millimole) of 2-thiopheneacetyl chloride in 5 milliliters of absolute methylene chloride was added slowly a slurry of 137 milligrams (0.5 millimole) of 7-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid and 86 milligrams (0.9 millimole) of triethylamine in 10 milliliters of absolute methylene chloride. The addition was carried out at -15° C., with stirring. After the addition, stirring was continued for two hours at -15° C. and for one and one-half hours at room temperature. The reaction mixture was then cooled and filtered to separate the precipitated solid. The solid, 80 milligrams, was analyzed on bioautogram. Bioautogram showed that approximately 50 percent of the sample was 7-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid and another 50 percent was the desired 7-(2-(2-thienyl)acetamido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid.

Workup

  1. additionThe addition
  2. customwas carried out at -15° C.
  3. additionAfter the addition
  4. stirringstirring
  5. temperatureThe reaction mixture was then cooled
  6. filtrationfiltered
  7. customto separate the precipitated solid

Sources & evidence

ORD record
ord-4554d0f13c0e4cd0840f45dea9b20c50
Source dataset
uspto-grants-1979_03
Patent number
US04145538

Reaction notes

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