Diethyl Ether → HCID 131715868, compound

HRID 1383123Notes

Reaction equation

HRID 1383123 reaction equation
Cl.Cl.[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][C:36](=[O:39])[NH:37][NH2:38])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[S:23][C:24]([CH3:27])=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[C:52]([O:55][C:56]1[CH:57]=[C:58]([CH:62]=[CH:63][C:64]=1[O:65][C:66](=[O:68])[CH3:67])[C:59]([Cl:61])=[O:60])(=[O:54])[CH3:53].CCOCC>C(Cl)Cl.CO>[ClH:61].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][C:36](=[O:39])[NH:37][NH:38][C:59](=[O:60])[C:58]2[CH:62]=[CH:63][C:64]([O:65][C:66](=[O:68])[CH3:67])=[C:56]([O:55][C:52](=[O:54])[CH3:53])[CH:57]=2)[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[S:23][C:24]([CH3:27])=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 140969484-(Chlorocarbonyl)-1,2-phenylene diacetateHCID 131715870HCID 131715870, compound

Product 1

HCID 131715868HCID 131715868, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 3 ml of methylene chloride was suspended 0.35 g (0.53 mmole) of 7-[2-(2-amino-1,3-thiazol-4-yl)-2-carbazoylmethoxyiminoacetamido]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl]-3-cephem-4-carboxylic acid.dihydrochloride obtained in Reference example 9 and the suspension was dissolved by adding 1.35 g (6.66 mmole) of N,O-bis(trimethylsilyl)acetamide. To the mixture was added 0.136 g (0.53 mmole) of 3,4-diacetoxybenzoic acid chloride and the mixture was stirred at room temperature for one hour. The mixture was poured into 200 ml of ether and added thereto a small amount of methanol while stirring. The resulting precipitates were collected by filtration, washed with water and then dried to obtain 0.42 g of the title compound. (Yield: 94.1%)

Workup

  1. customobtained in Reference example 9
  2. dissolutionthe suspension was dissolved
  3. additionadded
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-3f090d1bdc8a458e8d3091c8b6750117
Source dataset
uspto-grants-1989_02
Patent number
US04808711

Reaction notes

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