Ethanol → HCID 56999328, compound

HRID 1439971Notes

Reaction equation

HRID 1439971 reaction equation
[C:1]([O:4][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]CC2C=CC=CC=2)=O)[CH2:8][CH2:7][O:6]1)(=[O:3])[CH3:2].[CH2:29](O)[CH3:30]>[Pd]>[C:1]([O:4][C@H:5]1[C@@H:9]([NH:10][C:11](=[O:28])[C@H:12]([CH2:24][CH:25]([CH3:26])[CH3:27])[NH:13][C:14](=[O:16])[NH:10][C:11]2[C:29]3[C:30](=[CH:7][CH:8]=[CH:9][CH:5]=3)[CH:25]=[CH:24][CH:12]=2)[CH2:8][CH2:7][O:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 54054053HCID 54054053, compound

Product 1

HCID 56999328HCID 56999328, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2S, 3S )-2-Acetoxy-3-[[N-benzyloxycarbonyl-(L )leucyl]amino]tetrahydrofuran (3.2 g) was dissolved in ethanol (150 ml) followed by addition of palladium-on-carbon (5%, 1.5 g) and the catalytic hydrogenation was carried out at ambient temperature and atmospheric pressure. The catalyst was then filtered off and α-naphthyl isocyanate (1.5 g) was added to the filtrate. This mixture was stirred at room temperature for 3 hours. The reaction mixture was then concentrated under reduced pressure to obtain (2S,3S)-2-acetoxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]-tetrahydrofuran (chemical formula below) (2.95 g, 89%). As recrystallized from dichloromethane-methanolisopropyl ether, colorless crystals, m.p. 196°-198° C., optical rotation [α]D -51.8° (c=0.32, CHCl3). ##STR51##

Workup

  1. customwas carried out at ambient temperature
  2. filtrationThe catalyst was then filtered off
  3. additionα-naphthyl isocyanate (1.5 g) was added to the filtrate
  4. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-b3f746a2ef5d41b7b9d01239eb5f842f
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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