Water → Tert-butyl 7-amino-3-methoxymethyl-3-cephem-4-carboxylate

HRID 234183Notes

Reaction equation

HRID 234183 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:12][CH:13]1[C:30](=[O:31])[N:15]2[C:16]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:17]([CH2:20][O:21][CH3:22])[CH2:18][S:19][C@H:14]12.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:12][CH:13]1[C:30](=[O:31])[N:15]2[C:16]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[C:17]([CH2:20][O:21][CH3:22])[CH2:18][S:19][C@H:14]12

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 131713144Tert-butyl 7-amino-3-methoxymethyl-3-cephem-4-carboxylate tosylate

Product 1

HCID 67712488Tert-butyl 7-amino-3-methoxymethyl-3-cephem-4-carboxylateYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 7-amino-3-methoxymethyl -3-cephem-4-carboxylate tosylate (13.1 g) in methylene chloride (200 ml) was added water (100 ml), followed by adjusting to pH about 6 with an aqueous solution of sodium bicarbonate. After separating out the methylene chloride layer, the remaining aqueous solution was extracted with methylene chloride (50 ml). The combined methylene chloride solution was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then treated with an activated charcoal, followed by evaporation under reduced pressure to give tert-butyl 7-amino-3-methoxymethyl-3-cephem-4-carboxylate (5.7 g).

Workup

  1. customAfter separating out the methylene chloride layer
  2. extractionthe remaining aqueous solution was extracted with methylene chloride (50 ml)
  3. washThe combined methylene chloride solution was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additiontreated with an activated charcoal
  6. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-697b788dbc164a3c959e804926fbee80
Source dataset
uspto-grants-1997_01
Patent number
US05594132

Reaction notes

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