Hydrochloric Acid → HCID 57196224, compound

HRID 1975476Notes

Reaction equation

HRID 1975476 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16](=[O:33])[CH2:17][C@H:18]2[NH:21][C:20](=[O:22])[C@@H:19]2[C@H:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH3:24])[CH2:13][N:12]1[C:34]([O:36][CH2:37][C:38]1C=CC=C[CH:39]=1)=[O:35])=[O:10])[C:2]1C=CC=C[CH:3]=1.Cl>CO.[Pt]=O>[CH2:37]([O:36][C:34]([NH:12][CH2:13][CH:14]([CH2:15][NH:11][C:9]([O:8][CH2:1][CH:2]=[CH2:3])=[O:10])[C:16](=[O:33])[CH2:17][C@H:18]1[NH:21][C:20](=[O:22])[C@@H:19]1[C@H:23]([O:25][Si:26]([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:28])[CH3:27])[CH3:24])=[O:35])[CH:38]=[CH2:39]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57180843HCID 57180843, compound

Product 1

HCID 57196224HCID 57196224, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

To a solution of (3S,4R)-4-[2-{1,2-bis(benzyloxycarbonyl)pyrazolidin-4-yl}-2-oxoethyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (500 mg) and 1N hydrochloric acid (1.64 ml) in methanol (20 ml) was added platinum oxide (50 mg) under nitrogen atmosphere. The suspension was stirred under hydrogen atmosphere for 4 hours at room temperature. After then, the catalyst was filtered off and washed with water. After tetrahydrofuran (50 ml) and water (20 ml) was added, the pH was adjusted to 8.0 with saturated aqueous sodium bicarbonate in an ice bath and allyl chloroformate (348 ml) was added keeping pH at 8.0-8.5. After stirring for an hour at pH 8.0-8.5, the mixture was extracted three times with ethyl acetate. The combined organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel to give (3S,4R)-4 -[4-allyloxycarbonylamino-3-(N-allyloxycarbonylaminomethyl)-2-oxobutyl]-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-oxoazetidine (289 mg).

Workup

  1. filtrationAfter then, the catalyst was filtered off
  2. washwashed with water
  3. additionAfter tetrahydrofuran (50 ml) and water (20 ml) was added
  4. customthe pH was adjusted to 8.0 with saturated aqueous sodium bicarbonate in an ice bath
  5. additionallyl chloroformate (348 ml) was added
  6. stirringAfter stirring for an hour at pH 8.0-8.5
  7. extractionthe mixture was extracted three times with ethyl acetate
  8. washThe combined organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated under reduced pressure
  11. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-96587bac18874627a6538e78f689767e
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

Loading…