Acetyl chloride → HCID 131711042, compound

HRID 1678902Notes

Reaction equation

HRID 1678902 reaction equation
[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:22]([OH:24])=[O:23])=[C:10]([CH2:13][S:14][C:15]3[S:16][C:17]([CH2:20][NH2:21])=[N:18][N:19]=3)[CH2:11][S:12][C@H:7]12)=[S:4].[C:27](Cl)(=[O:29])[CH3:28]>C(N(CC)CC)C.O.O1CCCC1>[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:22]([OH:24])=[O:23])=[C:10]([CH2:13][S:14][C:15]3[S:16][C:17]([CH2:20][NH:21][C:27](=[O:29])[CH3:28])=[N:18][N:19]=3)[CH2:11][S:12][C@H:7]12)=[S:4]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 131711043HCID 131711043, compound

Product 1

HCID 131711042HCID 131711042, compoundYield 63.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

7-Methylthioacetamido-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (2.0 g.) was dissolved in a mixture of triethylamine (0.9 g.), water (20 ml.) and tetrahydrofuran (30 ml.). To this solution was added dropwise a solution of acetyl chloride (0.53 g.) in tetrahydrofuran (10 ml.) at 0°-5° C. The mixture was stirred at the same temperature for an hour, and then the tetrahydrofuran was distilled off under reduced pressure. The remaining solution was washed with ethyl acetate (100 ml. ), adjusted to pH1 with 10% hydrochloric acid and then extracted with ethyl acetate (200 ml.). The extract was washed with a saturated aqueous solution of sodium chloride, and the ethyl acetate was evaporated under reduced pressure. The residue was washed with acetone and then with ether to give 7-methylthioacetamido-3-(5-acetamidomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.4 g.). m.p. 145°-150° C (dec.).

Workup

  1. distillationthe tetrahydrofuran was distilled off under reduced pressure
  2. washThe remaining solution was washed with ethyl acetate (100 ml. )
  3. extractionextracted with ethyl acetate (200 ml.)
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. customthe ethyl acetate was evaporated under reduced pressure
  6. washThe residue was washed with acetone

Sources & evidence

ORD record
ord-9ca4a64002e44da49a33705e3472f427
Source dataset
uspto-grants-1978_03
Patent number
US04077965

Reaction notes

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