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 371207Notes

Reaction equation

HRID 371207 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-a682c8b711af4b8db5516d748bce7603
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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