Hydrochloric Acid → HCID 56611618, compound

HRID 1788802Notes

Reaction equation

HRID 1788802 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 2 ml of dichloromethane is dissolved 160 mg of (3S,4S)-4-cyano-3-triphenylmethylamino-2-azetidinone and, following addition of 154 mg of tetra-n-butylammonium hydrogen sulfate, 0.103 ml of 30% aqueous hydrogen peroxide and 0.68 ml of 1N sodium hydroxide are added under ice-cooling and stirring. The mixture is stirred vigorously for 30 minutes and poured into ice water containing 0.22 ml of 1N hydrochloric acid. After phase separation, the aqueous layer is extracted twice with chloroform. The organic layers are combined, washed with aqueous 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 75 mg of (3S,4S)-4-carbamoyl-3-triphenylmethylamino-2-azetidinone. The IR and NMR spectra of this compound are identical with those of the compound obtained in Example 17.

Workup

  1. additionare added under ice-
  2. temperaturecooling
  3. stirringThe mixture is stirred vigorously for 30 minutes
  4. customAfter phase separation
  5. extractionthe aqueous layer is extracted twice with chloroform
  6. washwashed with aqueous 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-ef45cd8e19f346a2939b798513a0897d
Source dataset
uspto-grants-1987_08
Patent number
US04684724

Reaction notes

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