Thiourea → HCID 177726839, compound

HRID 1463152Notes

Reaction equation

HRID 1463152 reaction equation
NC(N)=S.ClCC([NH:9][C:10]1[S:11][CH:12]=[C:13](/[C:15](=[N:49]/[O:50][CH3:51])/[C:16]([NH:18][CH:19]2[C:47](=[O:48])[N:21]3[C:22]([C:31]([O:33][CH:34]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:32])=[C:23]([CH:27]=[N:28][O:29][CH3:30])[C@@H:24]([CH3:26])[S:25][C@H:20]23)=[O:17])[N:14]=1)=O>O.O1CCCC1>[NH2:9][C:10]1[S:11][CH:12]=[C:13](/[C:15](=[N:49]/[O:50][CH3:51])/[C:16]([NH:18][CH:19]2[C:47](=[O:48])[N:21]3[C:22]([C:31]([O:33][CH:34]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[C:23]([CH:27]=[N:28][O:29][CH3:30])[C@@H:24]([CH3:26])[S:25][C@H:20]23)=[O:17])[N:14]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 178502645HCID 178502645, compound

Product 1

HCID 177726839HCID 177726839, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 84 mg of thiourea in 1 ml of H2O was added to a solution of 713 mg of diphenylmethyl 7-[2-(2-chloroacetylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylate in 10 ml of tetrahydrofuran, and the mixture was stirred overnight to distill off the solvent under reduced pressure. The residue was dissolved in CH2Cl2, washed with H2O and saturated aqueous NaCl solution, successively, and dried over MgSO4, followed by distilling off the CH2Cl2 under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.acetone (9:1) were collected to distill off the solvent, thus yielding 180 mg (28%) of diphenylmethyl 7-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylate.

Workup

  1. distillationto distill off the solvent under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with H2O and saturated aqueous NaCl solution
  4. dry with materialsuccessively, and dried over MgSO4
  5. distillationby distilling off the CH2Cl2 under reduced pressure
  6. additionThe residue was added on a column of silica gel
  7. washthe fractions eluted with CH2Cl2
  8. customacetone (9:1) were collected
  9. distillationto distill off the solvent

Sources & evidence

ORD record
ord-9db1b68165e241c4a75af2a91420566e
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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