Hydrochloric Acid → (2S,3R)-N-Benzyl-2,3-dihydroxybutanamide

HRID 459964Notes

Reaction equation

HRID 459964 reaction equation
[CH2:1]([NH:8][C:9]([C@@H:11]1[C@@H:15]([CH3:16])[O:14]C(C)(C)[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C(#N)C>[CH2:1]([NH:8][C:9](=[O:10])[C@@H:11]([OH:12])[C@H:15]([OH:14])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69028019HCID 69028019, compound

Product 1

HCID 69030861(2S,3R)-N-Benzyl-2,3-dihydroxybutanamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A flask was charged with 4.23 g (17.0 mmol) (4S,5R)-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide, 30 mL acetonitrile, and 17 mL 0.5 M aqueous hydrochloric acid solution. This mixture was stirred overnight at room temperature. The solution was made neutral by the addition of 1 M aqueous sodium hydroxide solution. The solvent was removed under reduced pressure, and the crude residue was dried in a vacuum oven. The dry, crude material was purified by column chromatography (20:1 dichloromethane/methanol) to give 3.03 g (85%) of the title compound as a white solid. MS (APCI) (m+1)/z 210.1.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dry with materialthe crude residue was dried in a vacuum oven
  3. customThe dry, crude material was purified by column chromatography (20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-606d7882f3ba4c38a3242e2b6f04f118
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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