Hydrochloric Acid → Hexanamide, 3-amino-N-cyclopropyl-2-hydroxy-, hydrochloride (1:1), (2S,3S)-

HRID 1928701Notes

Reaction equation

HRID 1928701 reaction equation
[ClH:1].[CH:2]1([NH:5][C:6](=[O:21])[C@@H:7]([OH:20])[C@@H:8]([NH:12]C(OC(C)(C)C)=O)[CH2:9][CH2:10][CH3:11])[CH2:4][CH2:3]1>O1CCOCC1>[ClH:1].[CH:2]1([NH:5][C:6](=[O:21])[C@@H:7]([OH:20])[C@@H:8]([NH2:12])[CH2:9][CH2:10][CH3:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68950941tert-Butyl ((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)carbamate

Product 1

HCID 25067786Hexanamide, 3-amino-N-cyclopropyl-2-hydroxy-, hydrochloride (1:1), (2S,3S)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 4 M 1,4-dioxane solution (60 mL) of hydrogen chloride, (2S,3S)—N-cyclopropyl-3-(t-butoxycarbonyl)amino-2-hydroxyhexanoic acid amide (4.5 g) was added. A solid of the product aggregated to form a lump after about 5 minutes, and the flowability of the reaction liquid worsened. After the disappearance of the starting material, the solvent was evaporated away with an evaporator to obtain a concentrated product of (2S,3S)—N-cyclopropyl-3-amino-2-hydroxyhexanoic acid amide hydrochloride (chemical purity: 89.8 area %).

Workup

  1. customto form a lump after about 5 minutes
  2. customthe flowability of the reaction liquid
  3. customAfter the disappearance of the starting material, the solvent was evaporated away with an evaporator

Sources & evidence

ORD record
ord-dd46bd71fb4b4373bd597a1fc00a832f
Source dataset
uspto-grants-2012_05
Patent number
US08183413B2

Reaction notes

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