p-Toluenesulfonic acid → HCID 86749309, compound

HRID 1439974Notes

Reaction equation

HRID 1439974 reaction equation
C(O[C@H:5]1[C@@H:9]([NH:10][C:11](=[O:28])[C@H:12]([CH2:24][CH:25]([CH3:27])[CH3:26])[NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:8][CH2:7][O:6]1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:40]([O:44][CH2:45][CH3:46])(=[O:43])[CH2:41][OH:42]>O1CCCC1>[CH2:17]([O:16][C:14]([NH:13][C@H:12]([C:11]([NH:10][C@H:9]1[CH2:8][CH2:7][O:6][CH:5]1[O:42][CH2:41][C:40]([O:44][CH2:45][CH3:46])=[O:43])=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12184Ethyl GlycolateHCID 54054053HCID 54054053, compound

Product 1

HCID 86749309HCID 86749309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (10 ml) was suspended (2S,3S)-2-acetoxy-3-[[N-benzyloxycarbonyl-(L)-leucyl]amino]tetrahydrofuran (0.8 g) and following addition of p-toluenesulfonic acid (0.02 g) and ethyl glycolate (5 ml), the mixture was stirred at room temperature for 5 hours. The reaction mixture was then concentrated under reduced pressure and the residue was chromatographed on a silica gel column, elution being carried out with ethyl acetate-hexane (1:1, v/v). From the eluate was obtained ethyl [(3S)-3-[[N-benzyloxycarbonyl-(L)-leucyl]amino]tetrahydrofuran-2-yl]oxyacetate (0.6 g) as an oil. This oil was dissolved in methanol (5 ml) followed by addition of potassium carbonate (0.1 g)-water (5 ml) and the mixture was stirred at room temperature for 3 hours. This reaction mixture was neutralized with 1N--HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried ((MgSO4) and the solvent was distilled off. The residue was dissolved in ethanol (20 ml) and following addition of 1N--NaOH (0.6 ml), the mixture was stirred at room temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure to provide sodium [(3S)-3-[[N-benzyloxycarbonyl-(L)-leucyl]amino]tetrahydrofuran-2-yl]oxyacetate (chemical formula below) (0.35 g, 41%). As recrystallized from methanol-ether, colorless powder, m.p. 125°-127° C., optical rotation [α]D +50.7° (c=0.33, dimethyl sulfoxide)

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was chromatographed on a silica gel column, elution

Sources & evidence

ORD record
ord-689be09ed42f4de58de08475ac94bac4
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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