Trisodium;borate;decahydrate → 3-Amino-3-methoxy-2-oxo-1-azetidinesulfonic acid tetrabutylammonium salt

HRID 371202Notes

Reaction equation

HRID 371202 reaction equation
O.O.O.O.O.O.O.O.O.O.B([O-])([O-])[O-].[Na+].[Na+].[Na+].[CH2:18]([N+:22]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21].[CH3:35][O:36][C:37]1([NH:46]C(OCC2C=CC=CC=2)=O)[CH2:40][N:39]([S:41]([O-:44])(=[O:43])=[O:42])[C:38]1=[O:45]>CO.[Pd]>[CH2:31]([N+:22]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:32][CH2:33][CH3:34].[NH2:46][C:37]1([O:36][CH3:35])[CH2:40][N:39]([S:41]([O-:44])(=[O:42])=[O:43])[C:38]1=[O:45]

Participants

5

Reactant 2

HCID 18377803Trisodium;borate;decahydrateHCID 1317142663-Methoxy-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt

Product 1

HCID 1317142653-Amino-3-methoxy-2-oxo-1-azetidinesulfonic acid tetrabutylammonium saltYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent3×

Procedure

A 4% sodium borate decahydrate in methanol solution (100 μl) is added to a suspension of 10% palladium on charcoal (30 mg) in methanol (2 ml), and the mixture is stirred under an atmosphere of hydrogen for 15 minutes. 3-Methoxy-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt (60 mg; see Example 49) in methanol (2 ml) is added and the mixture is vigorously stirred for 15 minutes under a hydrogen atmosphere. Catalyst is removed by filtration through Celite on a millipore filter (0.5 mμ), and solvent is removed from the filtrate in vacuo, and the residue is extracted with methylene chloride. Removal of solvent under reduced pressure yields 35 mg of the title compound, as an oil.

Workup

  1. stirringthe mixture is vigorously stirred for 15 minutes under a hydrogen atmosphere
  2. customCatalyst is removed by filtration through Celite on a millipore
  3. filtrationfilter (0.5 mμ), and solvent
  4. customis removed from the filtrate in vacuo
  5. extractionthe residue is extracted with methylene chloride
  6. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-03c9ffa8ebd94f2dbb32830d31a3b566
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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