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

HRID 1433326Notes

Reaction equation

HRID 1433326 reaction equation
C(O)(=O)[C@H](C1C=CC=CC=1)O.[CH:12]1([NH:15][C:16](=[O:24])[C@@H:17]([OH:23])[C@@H:18]([NH2:22])[CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13]1.[ClH:25]>C(OC(C)C)(=O)C>[ClH:25].[CH:12]1([NH:15][C:16](=[O:24])[C@@H:17]([OH:23])[C@@H:18]([NH2:22])[CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68535891(2s,3s)-n-Cyclopropyl-3-amino-2-hydroxyhexanamide (s)-mandelic acid salt

Product 1

HCID 25067786Hexanamide, 3-amino-N-cyclopropyl-2-hydroxy-, hydrochloride (1:1), (2S,3S)-Yield 98.2%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

38.7 g of (2S,3S)—N-cyclopropyl-3-amino-2-hydroxyhexanamide (S)-mandelic acid salt are suspended in 500 ml of isopropyl acetate and admixed with 11.8 g of 37% hydrochloric acid. After stirring at room temperature for 1 h, half of the solvent is distilled off in vacuo and replaced by fresh isopropyl acetate. After this has been repeated once more, the mixture is heated to 60° C., and the solid is filtered off and washed with warm isopropyl acetate. 25.0 g of (2S,3S)—N-cyclopropyl-3-amino-2-hydroxyhexanamide hydrochloride are obtained.

Workup

  1. distillationhalf of the solvent is distilled off in vacuo
  2. temperaturethe mixture is heated to 60° C.
  3. filtrationthe solid is filtered off
  4. washwashed with warm isopropyl acetate

Sources & evidence

ORD record
ord-df172adb186642b89bfbe74c67f554d5
Source dataset
uspto-grants-2009_11
Patent number
US07612237B2

Reaction notes

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