Methanol → HCID 137225462, compound

HRID 704515Notes

Reaction equation

HRID 704515 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:37][O:38][C:39]([C:42](=[O:45])[NH:43][NH2:44])([CH3:41])[CH3:40])[C:8]([NH:10][CH:11]2[C:35](=[O:36])[N:13]3[C:14]([C:32]([O-:34])=[O:33])=[C:15]([CH2:18][S:19][C:20]4[N:25]5[N:26]=[C:27]([CH2:29][OH:30])[N:28]=[C:24]5[N:23]=[C:22]([CH3:31])[CH:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[C:46]1(N)[C:51](F)=[C:50](F)C(F)=C(N)C=1F.Cl.Cl.CC[O:62][CH2:63][CH3:64].[C:65](=[O:68])([O-])O.[Na+:69].[CH3:70]O>O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:37][O:38][C:39]([C:42](=[O:45])[NH:43][N:44]=[CH:70][C:51]2[CH:50]=[CH:64][C:63]([OH:62])=[C:65]([OH:68])[CH:46]=2)([CH3:40])[CH3:41])[C:8]([NH:10][CH:11]2[C:35](=[O:36])[N:13]3[C:14]([C:32]([O-:34])=[O:33])=[C:15]([CH2:18][S:19][C:20]4[N:25]5[N:26]=[C:27]([CH2:29][OH:30])[N:28]=[C:24]5[N:23]=[C:22]([CH3:31])[CH:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+:69]

Participants

7

Reactant 5

HCID 887MethanolHCID 3283Diethyl EtherHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 516892Sodium BicarbonateHCID 131716558HCID 131716558, compound

Product 1

HCID 137225462HCID 137225462, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In 40 ml of methanol was dissolved 3.8 g of 7-[2-(2-amino-1,3-thiazol-4-yl)-2-(1-carbazoyl-1-methylethoxyimino)acetamido]-3-[(2-hydroxymethyl-5-methyl-s-triazolo[1,5-a]-pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylate.dihydrochloride, and then 1.03 g of protocatechuic aldehyde was added to the solution and the mixture was stirred at room temperature for 1.5 hours. The mixture was poured into 400 ml of ether and precipitates were collected by filtration, washed with ether and dried to obtain a powder. The powder was suspended in 100 ml of water and dissolved at pH 6 by addition of a 5% sodium hydrogencarbonate solution. After the resulting solution was adsorbed to 100 ml of HP 20 column filled with water, it was washed with water. Subsequently, the mixture was eluted with methanol - water. After condensation of fractions containing the title compound, the residue was freeze-dried to obtain 3.15 g of the title compound.

Workup

  1. customprecipitates
  2. filtrationwere collected by filtration
  3. washwashed with ether
  4. customdried
  5. customto obtain a powder
  6. washwas washed with water
  7. washSubsequently, the mixture was eluted with methanol - water
  8. customAfter condensation of fractions

Sources & evidence

ORD record
ord-2932ab0ad9ed4c13bed8d9b38e9dca55
Source dataset
uspto-grants-1991_01
Patent number
US04987129

Reaction notes

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