Hydrochloric Acid → HCID 178520244, compound

HRID 1995786Notes

Reaction equation

HRID 1995786 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O-:23])=[O:22])=[C:15]([CH2:19]Cl)[CH2:16][S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:26]1[C:30]([SH:31])=[N:29][N:28]=[N:27]1.CN(C)C=O.Cl.C(N([CH2:43][CH3:44])CC)C>>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O:23][CH:7]([C:44]4[CH:43]=[CH:21][CH:14]=[CH:15][CH:16]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[O:22])=[C:15]([CH2:19][S:31][C:30]4[NH:29][N:28]=[N:27][N:26]=4)[CH2:16][S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 1317130867-(2-Phenylacetamido)-3-chloromethyl-3-cephem-4-carboxylate-1-oxideHCID 178527994HCID 178527994, compound

Product 1

HCID 178520244HCID 178520244, compoundYield 139.8%

Procedure

A mixture of benzyhydryl 7-(2-phenylacetamido)-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (70.0 g), 1H-tetrazole-5-thiol (15.6 g) and N,N-dimethylformamide (700 ml) was stirred to give a homogeneous solution and thereto was added triethylamine (32.1 g), keeping the temperature at 20° to 30° C. The resulting solution was stirred for 40 minutes at room temperature. After the reaction mixture was added to ice water (2.8 l), the mixture was adjusted to pH 2.0 with 10% hydrochloric acid and then filtered. The filter cake was washed with water and dried over phosphorus pentoxide under reduced pressure to give benzhydryl 7-(2-phenylacetamido)-3-(1H-tetrazole-5-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (78.8 g).

Workup

  1. customto give a homogeneous solution
  2. customat 20° to 30° C
  3. stirringThe resulting solution was stirred for 40 minutes at room temperature
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-84542addd9eb472abc6fa8c505c0e92b
Source dataset
uspto-grants-1983_09
Patent number
US04405617

Reaction notes

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