Water → HCID 178502830, compound

HRID 483019Notes

Reaction equation

HRID 483019 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:52]/[O:53][CH3:54])/[C:27]([NH:29][C@@H:30]2[C:50](=[O:51])[N:32]3[C:33]([C:47]([OH:49])=[O:48])=[C:34]([CH2:37][S:38][C:39]4[N:43]([NH:44][CH:45]=[O:46])[N:42]=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.O1CCCC1.CCOCC>C(O)=O>[CH:47]([OH:49])=[O:48].[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:52]/[O:53][CH3:54])/[C:27]([NH:29][C@@H:30]2[C:50](=[O:51])[N:32]3[C:33]([C:47]([OH:49])=[O:48])=[C:34]([CH2:37][S:38][C:39]4[N:43]([NH:44][CH:45]=[O:46])[N:42]=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 13261986HCID 13261986, compound

Product 1

HCID 178502830HCID 178502830, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2.60 g of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-formamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid were dissolved in 10 ml of 80% formic acid, and the solution was stirred at room temperature for one hour. 40 ml of water were added to the reaction solution, and insoluble materials were removed by filtration. The filtrate was condensed at a temperature below 40° C. under reduced pressure. One ml of tetrahydrofuran and 2 ml of ether were added to the residue, and the resultant precipitates were collected by filtration. 0.72 g of 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-formamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid formate thus obtained as pale yellow powder were suspended in 8 ml of ethanol, and the suspension was stirred at 50° C. for 30 minutes. After cooling, the precipitates were collected by filtration. 0.53 g of 7β -[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-formamido-1H-tetrazol-5-yl)thiomethyl]-3cephem-4-carboxylic acid was thereby obtained as pale yellow powder.

Workup

  1. customwere removed by filtration
  2. customcondensed at a temperature below 40° C. under reduced pressure
  3. customthe resultant precipitates
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-000bf08ecc1b4554a7be27dcc2f6dcde
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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