Water → HCID 57319928, compound

HRID 1439970Notes

Reaction equation

HRID 1439970 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]1[CH2:24][CH2:23][O:22][CH:21]1[OH:25])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[C:27](OC(=O)C)(=[O:29])[CH3:28]>CN(C)C1C=CN=CC=1>[C:27]([O:25][CH:21]1[C@@H:20]([NH:19][C:17](=[O:18])[C@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:24][CH2:23][O:22]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 56984114HCID 56984114, compound

Product 1

HCID 57319928HCID 57319928, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

(3S)-3-[[N-tert-Butoxycarbonyl-(L)-phenylalanyl]amino]-2-hydroxytetrahydrofuran (0.1 g) was dissolved in acetic anhydride (3 ml) followed by addition of 4-dimethylaminopyridine (DMAP) (0,012 g) and the mixture was stirred at room temperature for 12 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with 10% aqueous citric acid, water, saturated aqueous sodium hydrogen carbonate, and saturated aqueous sodium chloride in the order mentioned and dried (MgSO4) and the solvent was distilled off to give (3S)-2-acetoxy-3-[[N-tert-butoxycarbonyl-(L)-phenylalanyl]amino]tetrahydrofuran (chemical formula below) (0,035 g, 29%). This product was recrystallized from ethyl acetate-hexane. Colorless crystals, m.p. 156°-157° C. Optical rotation [α]D -49.9° (C=0.15, CHCl3). ##STR45##

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 10% aqueous citric acid, water, saturated aqueous sodium hydrogen carbonate, and saturated aqueous sodium chloride in the order
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c5190a14fa354b92acba335c265febe9
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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