Hydrochloric Acid → HCID 56611618, compound

HRID 638125Notes

Reaction equation

HRID 638125 reaction equation
[C:1]([C@H: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+].Cl>ClCCl.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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 13232655HCID 13232655, compound

Product 1

HCID 56611618HCID 56611618, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In 12 ml of dichloromethane is dissolved 1.06 g of (3S,4S)-4-cyano-3-triphenylmethylamino-2-azetidinone and, following addition of 1.02 g of tetra-n-butylammonium hydrogen sulfate, 0.68 ml of 30% aqueous hydrogen peroxide and 4.5 ml of 1 N sodium hydroxide are added under ice-cooling and stirring. The mixture is stirred vigorously for 50 minutes and poured into ice water containing 1.3 ml of 1 N hydrochloric acid. After phase separation, the aqueous layer is extracted twice with chloroform. The organic layers are combined and washed with an aqueous solution of sodium thiosulfate and sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is chromatographed on a silica gel column [eluant: chloroform-ethyl acetate-methanol (50:50:5)] to give 0.223 g of (3S,4S)-4-carbamoyl-3-triphenylmethylamino-2-azetidinone.

Workup

  1. additionare added under ice-
  2. temperaturecooling
  3. stirringThe mixture is stirred vigorously for 50 minutes
  4. customAfter phase separation
  5. extractionthe aqueous layer is extracted twice with chloroform
  6. washwashed with an aqueous solution of sodium thiosulfate and sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is chromatographed on a silica gel column [eluant: chloroform-ethyl acetate-methanol (50:50:5)]

Sources & evidence

ORD record
ord-9486349a07974675820e37066a4a5dad
Source dataset
uspto-grants-1985_12
Patent number
US04560508

Reaction notes

Loading…