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Sodium Hydroxide → Sodium 7beta-(p-methoxybenzyloxycarbonylamino)-3-hydroxymethyl-3-cephem-4-carboxylate

HRID 1649753
Notes
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Reaction equation

HRID 1649753 reaction equation
[NH2:1][C@@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]12.[OH-].[Na+:17].[CH3:18][O:19][C:20]1[CH:38]=[CH:37][C:23]([CH2:24][O:25][C:26](SC2C=C(C)C=C(C)N=2)=[O:27])=[CH:22][CH:21]=1.O1CCOCC1>O.C(OCC)(=O)C>[CH3:18][O:19][C:20]1[CH:38]=[CH:37][C:23]([CH2:24][O:25][C:26]([NH:1][C@@H:2]2[C:14](=[O:15])[N:4]3[C:5]([C:11]([O-:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]23)=[O:27])=[CH:22][CH:21]=1.[Na+:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 11031679(6R-trans)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 13505496S-p-methoxybenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyridine

Product 1

HCID 67868099Sodium 7beta-(p-methoxybenzyloxycarbonylamino)-3-hydroxymethyl-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In 50 ml of water is suspended 2.30 g of 7β-amino-3-hydroxymethyl-3-cephem-4-carboxylic acid and the suspension is adjusted to pH 8.5 with 1N-aqueous sodium hydroxide solution, whereupon a clear solution is obtained. To this solution are added 4.56 g of S-p-methoxybenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyridine and 50 ml of dioxane and the mixture is stirred at room temperature for 7 hours. The reaction mixture is diluted with water and ethyl acetate and the water layer is separated and concentrated under reduced pressure. The residue is subjected to XAD-II (500 ml) column chromatography and after the column is washed with water, elution is carried out with 10% (v/v) ethanol. The eluate is concentrated under reduced pressure and freeze-dried to give 1.63 g of sodium 7β-(p-methoxybenzyloxycarbonylamino)-3-hydroxymethyl-3-cephem-4-carboxylate as colorless powders.

Workup

  1. customis obtained
  2. customthe water layer is separated
  3. concentrationconcentrated under reduced pressure
  4. washafter the column is washed with water, elution
  5. concentrationThe eluate is concentrated under reduced pressure
  6. customfreeze-dried

Sources & evidence

ORD record
ord-769264b41c0d43e381685c7878292218
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04921851

Reaction notes

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