HCID 56999328, compound → HCID 70115155, compound

HRID 1439977Notes

Reaction equation

HRID 1439977 reaction equation
[C:1]([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>CO.Cl>[CH3:1][O:4][CH:5]1[C@@H: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

4

Reactant 1

HCID 56999328HCID 56999328, compound

Product 1

HCID 70115155HCID 70115155, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

In methanol (20 ml) was suspended (2S,3S)-2-acetoxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]tetrahydrofuran (0.1 g) and following addition of concentrated hydrochloric acid (5 drops), the mixture was stirred at room temperature for 1 hour. The reaction mixture was then concentrated under reduced pressure to give (3S)-2-methoxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]-tetrahydrofuran (chemical structure below) (0.08 g, 87%). As recrystallized from dichloromethane-isopropyl ether, colorless crystals, m.p. 184°-185° C., optical rotation [α]D +13.0° (C=0.27, CHCl3).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e5faf60d2b844e5bda0e70c02e3b251
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

Loading…