HCID 57117802, compound → HCID 57001201, compound

HRID 1439975Notes

Reaction equation

HRID 1439975 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([NH:10][C:11](=[O:37])[C@H:12]([CH2:33][CH:34]([CH3:36])[CH3:35])[NH:13][C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([NH:21]C(OCC3C=CC=CC=3)=O)=[CH:17][CH:16]=2)[CH2:8][CH2:7][O:6]1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:4][C@H:5]1[C@@H:9]([NH:10][C:11](=[O:37])[C@H:12]([CH2:33][CH:34]([CH3:35])[CH3:36])[NH:13][C:14](=[O:32])[C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:8][CH2:7][O:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 57117802HCID 57117802, compound

Product 1

HCID 57001201HCID 57001201, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In ethanol (100 ml) was dissolved (2S,3S)-2-acetoxy-3-[[N-[4-(N-benzyloxycarbonylamino)benzoyl]-(L)-leucyl]amino]tetrahydrofuran (1.0 g) and following addition of palladium-on-carbon (5%, 0.7 g), the catalytic hydrogenation was carried out at ambient temperature and atmospheric pressure. The catalyst was then filtered off and the filtrate was concentrated under reduced pressure to provide (2S,3S)-2-acetoxy-3-[[N-(4-aminobenzoyl)-(L)-leucyl]amino]tetrahydrofuran (chemical formula below) (0.61 g, 81%). As recrystallied from dichloromethane-isopropyl ether, colorless crystals, m.p. 148°-150° C. optical rotation [α]D -61.3° (C=0.29, CHCl3). ##STR68##

Workup

  1. customwas carried out at ambient temperature
  2. filtrationThe catalyst was then filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dfc259b23b4e45fc895e729fc36d2455
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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