Thiourea → HCID 141552859, compound

HRID 1194164Notes

Reaction equation

HRID 1194164 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[O:59][CH2:60][C:61]([O:63][CH:64]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:62])/[C:27]([NH:29][C@@H:30]2[C:56](=[O:57])[N:32]3[C:33]([C:44]([O:46][CH2:47][C:48]4[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=4)=[S:45])=[C:34]([CH2:37][CH2:38][O:39]C(=O)CCl)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC(N)=S>CN(C)C(=O)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[O:59][CH2:60][C:61]([O:63][CH:64]([C:71]2[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=2)[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:62])/[C:27]([NH:29][C@@H:30]2[C:56](=[O:57])[N:32]3[C:33]([C:44]([O:46][CH2:47][C:48]4[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=4)=[S:45])=[C:34]([CH2:37][CH2:38][OH:39])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 178491562HCID 178491562, compound

Product 1

HCID 141552859HCID 141552859, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
20 °C

Procedure

(d-1) To a solution of 1.24 g (1.12 mM) of p-methoxybenzyl 7β-{α-(2-tritylaminothiazole-4-yl)-α-[(Z)-benzhydryloxycarbonylmethoxyimino]acetamido}-3-(2-chloroacetyloxy)ethylthio-3-cephem-4-carboxylate, in 7 ml of N,N-dimethylacetamide was added 171 mg (2.24 mM) of thiourea, and the mixture was stirred at 20° C. for 16 hours. Then, the reaction mixture was poured into 20 ml of ice-water and extracted with 30 ml of ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution (10 ml×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent; benzene:acetone=5:1), and then crystallized from diethyl ether to give 780 mg of p-methoxybenzyl 7β-{α-(2-tritylaminothiazole-4-yl)-α-[(Z)-benzhydryloxycarbonylmethoxyimino]acetamido}-3-(2-hydroxy)ethylthio-3-cephem-4-carboxylate

Workup

  1. extractionextracted with 30 ml of ethyl acetate
  2. washthe extract was washed with a saturated aqueous sodium chloride solution (10 ml×3)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (eluent; benzene:acetone=5:1)
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-1880911afaf34a99b991ee6d834f5492
Source dataset
uspto-grants-1989_03
Patent number
US04812562

Reaction notes

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