Potassium Carbonate → HCID 54268157, compound

HRID 1439972Notes

Reaction equation

HRID 1439972 reaction equation
C([O:4][C@H:5]1[C@@H:9]([NH:10][C:11](=[O:31])[C@H:12]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH:13][C:14](=[O:26])[NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][O:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:4][CH:5]1[CH:9]([NH:10][C:11](=[O:31])[C@H:12]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:13][C:14](=[O:26])[NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][O:6]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 56999328HCID 56999328, compound

Product 1

HCID 54268157HCID 54268157, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

(2S,3S)-2-Acetoxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]tetrahydrofuran (2.9 g) was suspended in methanol (50 ml) followed by addition of a solution of potassium carbonate (0.94 g) in water (5 ml) under ice-cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4) and the solvent was distilled off to give 2-hydroxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]tetrahydrofuran (chemical formula below) (1.95 g, 72%). As recrystallized from dichloromethane-methanolisopropyl ether, colorless crystals, m.p. 177°-178° C., optical rotation [α]D +29.5° (c=0.25, dimethyl sulfoxide).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-912fef6a93f742b4a69d202dedd19167
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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