Methanol → HCID 137225462, compound

HRID 1032227Notes

Reaction equation

HRID 1032227 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 conensation 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. additionAfter conensation of fractions containing the title compound
  9. customthe residue was freeze-dried

Sources & evidence

ORD record
ord-c39da1e70a6e4ea59703ed39fea2cb8b
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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