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

HRID 1173780
Notes
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Reaction equation

HRID 1173780 reaction equation
[CH:1]1([NH:4][C:5]([C@H:7]2[O:11]C(C(C)C)=[N:9][C@H:8]2[CH2:15][CH2:16][CH3:17])=[O:6])[CH2:3][CH2:2]1.[ClH:18]>CC(C)=O>[ClH:18].[CH:1]1([NH:4][C:5](=[O:6])[C@@H:7]([OH:11])[C@@H:8]([NH2:9])[CH2:15][CH2:16][CH3:17])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59203385(4S,5S)-N-Cyclopropyl-2-isopropyl-4-propyl-4,5-dihydro-1,3-oxazole-5-carboxamide

Product 1

HCID 25067786Hexanamide, 3-amino-N-cyclopropyl-2-hydroxy-, hydrochloride (1:1), (2S,3S)-Yield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

(4S,5S)—N-Cyclopropyl-2-isopropyl-4-propyl-4,5-dihydro-1,3-oxazole-5-carboxamide (3.11 g, 8.7 mmol), acetone (15 ml) and concentrated hydrochloric acid (1.39 g, 1.5 equivalents) were mixed, and the mixture was stirred at 50° C. for 39 hours. The solvent was evaporated away under reduced pressure. Isopropanol (10 ml) was added, and the mixture was concentrated. The same operation was repeated again. Methanol (2.7 ml) was added to the obtained solid, and the mixture was stirred at 60° C. for 1 hour. Ethyl acetate (20 ml) was gradually added thereto dropwise. After the addition, the mixture was gradually cooled to 5° C. The precipitated crystal was collected by filtration, and dried under reduced pressure to obtain the title compound as a white crystal (1.36 g, yield: 72%).

Workup

  1. customThe solvent was evaporated away under reduced pressure
  2. additionIsopropanol (10 ml) was added
  3. concentrationthe mixture was concentrated
  4. additionMethanol (2.7 ml) was added to the obtained solid
  5. stirringthe mixture was stirred at 60° C. for 1 hour
  6. additionEthyl acetate (20 ml) was gradually added
  7. additionAfter the addition
  8. temperaturethe mixture was gradually cooled to 5° C
  9. filtrationThe precipitated crystal was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-255e10ca155b4a47adaac23f262bce7b
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834190B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes