HCID 57242274, compound → HCID 22859256, compound

HRID 1439973Notes

Reaction equation

HRID 1439973 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([NH:10][C:11](=[O:26])[C@H:12]([CH:23]([CH3:25])[CH3:24])[NH:13][C:14](=[O:22])[CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:8][CH2:7][O:6]1)(=O)C>CO.Cl>[CH3:1][O:4][C@@H:5]1[C@@H:9]([NH:10][C:11](=[O:26])[C@H:12]([CH:23]([CH3:24])[CH3:25])[NH:13][C:14](=[O:22])[CH:15]([CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH3:21])[CH2:8][CH2:7][O:6]1

Participants

4

Reactant 1

HCID 57242274HCID 57242274, compound

Product 1

HCID 22859256HCID 22859256, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

In methanol (50 ml) was suspended (2S, 3S)-2-acetoxy-3-[[N-valproyl-(L)-valyl]amino]tetrahydrofuran (0.55 g) followed by addition of concentrated hydrochloric acid (5 drops) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then concentrated under reduced pressure to obtain (2S,3S)-2-methoxy-3-[[N-valproyl-(L)-valyl]amino]tetrahydrofuran (chemical structure below) (0.38 g, 72%). As recrystallized from ethyl acetate, colorless crystals, m.p. 150°-156° C., optical rotation [α]D+ 18.5° (c=0.50, CHCl3).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d375edf9ebb4e4c821c0d563805560b
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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