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

HRID 1928705
Notes
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Reaction equation

HRID 1928705 reaction equation
[CH:1]1([NH:4][C:5](=[O:20])[C@@H:6]([OH:19])[C@@H:7]([NH:11]C(OC(C)(C)C)=O)[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1.[ClH:21]>C(O)(C)C>[ClH:21].[CH:1]1([NH:4][C:5](=[O:20])[C@@H:6]([OH:19])[C@@H:7]([NH2:11])[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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)-Yield 80.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

Isopropanol (250 mL) was added to (2S,3S)—N-cyclopropyl-3-(tert-butoxycarbonyl)amino-2-hydroxyhexanoic acid amide (26.5 g, 92.54 mmol), and the mixture was heated up to about 60° C. To the solution, 35% hydrochloric acid aqueous solution (14.5 g, 138.8 mmol) was dropwise added, and the mixture was stirred for 24 hours. After the disappearance of the starting material, the reaction liquid for the remove of Boc function group was cooled from 60° C. to 2° C. at a constant cooling rate, taking about 6 hours. As a result, no solid aggregated and the flowability thereof was good. The precipitated crystals were collected by filtration under reduced pressure, using a Kiriyama funnel (diameter 6 cm, filter pore size 4 μm). At the time, the filterability was good and the time for the separation of the crystals from the mother liquid was about 60 seconds. By the isolation and drying in vacuum, (2S,3S)—N-cyclopropyl-3-amino-2-hydroxyhexanoic acid amide hydrochloride (16.53 g) was obtained as white crystals (yield: 80 mol %, isopropanol content: no isopropanol detected, chemical purity: 100.0 area %, optical purity: 100% ee).

Workup

  1. customAfter the disappearance of the starting material, the reaction liquid for the
  2. customremove of Boc function group
  3. temperaturewas cooled from 60° C. to 2° C. at a constant cooling rate
  4. waittaking about 6 hours
  5. filtrationThe precipitated crystals were collected by filtration under reduced pressure
  6. filtrationa Kiriyama funnel (diameter 6 cm, filter pore size 4 μm)
  7. customthe time for the separation of the crystals from the mother liquid
  8. waitwas about 60 seconds
  9. customBy the isolation and drying in vacuum

Sources & evidence

ORD record
ord-a5ad5804711d4589b033ab5ce1d707a7
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183413B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes