Hydrogen chloride-ethyl acetate → HCID 69081988, compound

HRID 1510251Notes

Reaction equation

HRID 1510251 reaction equation
[NH:1]([C@@H:8]([CH2:24][O:25]C(C)(C)C)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[ClH:36]>C(OCC)(=O)C.CCCCCC>[ClH:36].[ClH:36].[NH:1]([C@@H:8]([CH2:24][OH:25])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 69082361HCID 69082361, compound

Product 1

HCID 69081988HCID 69081988, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (2S)-2-anilino-3-tert-butoxy-N-[4-(4-pyridinyl)phenyl]propanamide (70 mg) in ethyl acetate (0.42 mL) was added 4N hydrogen chloride-ethyl acetate (1.8 mL) and the mixture was stirred at ambient temperature for 5 hours. The resulting mixture was diluted with n-hexane (2.5 mL) and the solid was collected by filtration and washed with n-hexane (2.5 mL) to give (2S)-2-anilino-3-hydroxy-N-[4-(4-pyridinyl)phenyl]propanamide dihydrochloride (72 mg) as an off-white solid.

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with n-hexane (2.5 mL)

Sources & evidence

ORD record
ord-9a34b2c12a524483a4cc7486f6c4b955
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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