Hydrochloric Acid → HCID 131713451, compound

HRID 1904122Notes

Reaction equation

HRID 1904122 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:60])[C:32]([C:35]3[N:36]=[C:37]([NH:40][C:41]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[S:38][CH:39]=3)=[N:33][OH:34])[C:28](=[O:61])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].BrC[C:64]1[CH:74]=[CH:73][CH:72]=[C:66]2[C:67]([NH:69][C:70](=[O:71])[C:65]=12)=[O:68].[C:75](=O)([O-])[O-].[K+].[K+].Cl>C(OCC)(=O)C.CS(C)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:60])[C:32]([C:35]3[N:36]=[C:37]([NH:40][C:41]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[S:38][CH:39]=3)=[N:33][O:34][CH2:75][N:69]3[C:70](=[O:71])[C:65]4=[CH:64][CH:74]=[CH:73][CH:72]=[C:66]4[C:67]3=[O:68])[C:28](=[O:61])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:13])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 22179298HCID 22179298, compoundHCID 131712161Diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate

Product 1

HCID 131713451HCID 131713451, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.085 g of the product of Step B, 0.12 g of bromomethyl phthalimide, 0.069 g of potassium carbonate and 0.4 ml of dimethylsulfoxide was vigorously stirred for 15 minutes at room temperature and 10 ml of 0.1 N hydrochloric acid were added thereto. The mixture was vacuum filtered and the product was washed with water and dried to obtain 0.124 g of raw product. The latter was dissolved in 1 ml of ethyl acetate and the solution was treated with activated carbon and the solvent was distilled off. The residue was efflorescenced with ether and the mixture was vacuum filtered to obtain 0.075 g of syn isomer of diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-phthalimidomethyloxyimino-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. filtrationfiltered
  2. washthe product was washed with water
  3. customdried
  4. customto obtain 0.124 g of raw product
  5. additionthe solution was treated with activated carbon
  6. distillationthe solvent was distilled off
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e7203e0e656d45e7b59c27d7493be04e
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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