tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonate → tetrabutylammonium (S)-3-amino-2-oxoazetidine-1-sulfonate

HRID 371200Notes

Reaction equation

HRID 371200 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].[O:18]=[C:19]1[C@@H:22]([NH:23]C(OCC2C=CC=CC=2)=O)[CH2:21][N:20]1[S:34]([O-:37])(=[O:36])=[O:35]>CN(C)C=O.[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].[NH2:23][C@H:22]1[CH2:21][N:20]([S:34]([O-:37])(=[O:36])=[O:35])[C:19]1=[O:18]

Participants

4

Reactant 1

HCID 13575530tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonate

Product 1

HCID 13309502tetrabutylammonium (S)-3-amino-2-oxoazetidine-1-sulfonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

(S)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt (2 g; see Example 4) is dissolved in 100 ml of dimethylformamide and hydrogenated for about 30 minutes with 1 g of palladium on charcoal (10%) as catalyst. The catalyst is filtered off and the dimethylformamide is removed leaving the title compound as an oil.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe dimethylformamide is removed

Sources & evidence

ORD record
ord-927e98170bab41709e748a4847a8053a
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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