3-Methoxy-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt → 3-Amino-3-methoxy-2-oxo-1-azetidinesulfonic acid tetrabutylammonium salt

HRID 867638Notes

Reaction equation

HRID 867638 reaction equation
[CH2:1]([N+:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH3:18][O:19][C:20]1([NH:29]C(OCC2C=CC=CC=2)=O)[CH2:23][N:22]([S:24]([O-:27])(=[O:26])=[O:25])[C:21]1=[O:28]>CO.[Pd]>[CH2:14]([N+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:15][CH2:16][CH3:17].[NH2:29][C:20]1([O:19][CH3:18])[CH2:23][N:22]([S:24]([O-:27])(=[O:25])=[O:26])[C:21]1=[O:28]

Participants

4

Reactant 1

HCID 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 104.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(±)-3-Methoxy-3-[[(phenylmethoxy)carbonyl]amino]-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt (143 mg, see Example 49) is dissolved in 15 ml of dry methanol. Na2B4O7.10H2O (12 mg, 0.1 equiv.) is added, followed by 10% palladium on carbon (72 mg). The mixture is hydrogenated at one atmosphere pressure for 15 minutes. The catalyst is removed by filtration and the filtrate evaporated in vacuo, yielding 114 mg of the title compound.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-a8d0d81a050a49ec9566d8c09460ea6c
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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