Hydrogen Peroxide → HCID 56611618, compound

HRID 1788804Notes

Reaction equation

HRID 1788804 reaction equation
[C:1]([CH:3]1[NH:6][C:5](=[O:7])[C@H:4]1[NH:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:2].[OH:28]O.[OH-].[Na+]>C(Cl)(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([C@H:3]1[NH:6][C:5](=[O:7])[C@H:4]1[NH:8][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:28])[NH2:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 13232653HCID 13232653, compound

Product 1

HCID 56611618HCID 56611618, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6212ChloroformSolvent

Procedure

In 40 ml of chloroform is dissolved 3.54 g of (3S,4RS)-4-cyano-3-tritylamino-2-azetidinone as obtained in Example 20 and, following addition of 3.4 g of tetra-n-butylammonium hydrogen sulfate, 2.3 g of 30% hydrogen peroxide and 15 ml of 1N sodium hydroxide are added under ice-cooling and stirring. The mixture is stirred vigorously for 30 minutes and the organic layer is taken out, while the aqueous layer is extracted twice with chloroform. The organic layers are combined, washed with water and treated in the same manner as Example 19 to give 0.76 g of (3S,4S)-4-carbamoyl-3-tritylamino-2-azetidinone. The IR and NMR spectra of this compound are identical with those of the compound obtained in Example 17.

Workup

  1. customas obtained in Example 20
  2. additionare added under ice-
  3. temperaturecooling
  4. stirringThe mixture is stirred vigorously for 30 minutes
  5. extractionis extracted twice with chloroform
  6. washwashed with water
  7. additiontreated in the same manner as Example 19

Sources & evidence

ORD record
ord-f19b343e797049888b9b1649d2bc69eb
Source dataset
uspto-grants-1987_08
Patent number
US04684724

Reaction notes

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