Hydrochloric Acid → HCID 56611618, compound

HRID 638127Notes

Reaction equation

HRID 638127 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].[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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 peroxide and 0.68 ml of 1 N sodium hydroxide are added under ice-cooling and stirring. The mixtire is stirred vigorously for 30 minutes and poured into ice water containing 0.22 ml of 1 N 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 mixtire 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-8ee95ff681b044c4818b87d31fc700ff
Source dataset
uspto-grants-1985_12
Patent number
US04560508

Reaction notes

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