Hydrochloric Acid → HCID 70586710, compound

HRID 1678903Notes

Reaction equation

HRID 1678903 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:29](=[O:30])[N:12]2[C:13]([C:26]([OH:28])=[O:27])=[C:14]([CH2:17][S:18][C:19]3[S:20][C:21]([CH2:24][NH2:25])=[N:22][N:23]=3)[CH2:15][S:16][C@H:11]12)=[O:8].[CH3:31][S:32](Cl)(=[O:34])=[O:33].Cl>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:29](=[O:30])[N:12]2[C:13]([C:26]([OH:28])=[O:27])=[C:14]([CH2:17][S:18][C:19]3[S:20][C:21]([CH2:24][NH:25][S:32]([CH3:31])(=[O:34])=[O:33])=[N:22][N:23]=3)[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 70584193HCID 70584193, compound

Product 1

HCID 70586710HCID 70586710, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(2-Thienyl)acetamido-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (2.46 g.) was suspended in methylene chloride (100 ml.). To the suspension was added bis(trimethylsilyl)acetamido (4.06 g.) and the mixture was stirred to give a solution. To the solution was added methanesulfonyl chloride (1.15 g.) and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was added to 5% hydrochloric acid at 0°-5° C. White precipitates in the solution were collected by filtration, dried and then recrystallized with aqueous acetone to give 7-(2-thienyl)acetamido-3-(5-mesylaminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (910 mg.). m.p. 139°-145° C (dec.).

Workup

  1. additionTo the suspension was added bis(trimethylsilyl)acetamido (4.06 g.)
  2. customto give a solution
  3. stirringthe mixture was stirred at room temperature for 3 hrs
  4. customWhite precipitates in the solution
  5. filtrationwere collected by filtration
  6. customdried
  7. customrecrystallized with aqueous acetone

Sources & evidence

ORD record
ord-a6fbfbd469904da5b8cdddcf69ec5ce7
Source dataset
uspto-grants-1978_03
Patent number
US04077965

Reaction notes

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