Hydrogen chloride-ethyl acetate → N-[(1S)-2-({1-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]acetamide

HRID 2368071Notes

Reaction equation

HRID 2368071 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([N:14]4[CH2:19][CH2:18][CH:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=O)[O:26]C(C)(C)C)[CH3:23])[CH2:16][CH2:15]4)=[N:11][C:10]=3[CH:32]=2)[CH2:3][CH2:2]1.Cl.[C:34](OCC)(=O)C>>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([N:14]4[CH2:19][CH2:18][CH:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:26])[CH3:34])[CH3:23])[CH2:16][CH2:15]4)=[N:11][C:10]=3[CH:32]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86658694HCID 86658694, compound

Product 1

HCID 53492188N-[(1S)-2-({1-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]acetamide

Procedure

To tert-butyl [(1S)-2-({1-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate (30.1 g) was added 4M hydrogen chloride/ethyl acetate (200 mL), and the mixture was stirred at room temperature for 30 min. After stirring, the mixture was concentrated. Pyridine (100 mL) and acetic anhydride (100 mL) were added to the residue, and the mixture was stirred at room temperature for 15 min. After concentration, the residue was purified by silica gel chromatography (NH, hexane/ethyl acetate), and the obtained crystals were recrystallized from hexane/ethyl acetate to give the title compound (17.4 g) as white crystals.

Workup

  1. stirringAfter stirring
  2. concentrationthe mixture was concentrated
  3. additionPyridine (100 mL) and acetic anhydride (100 mL) were added to the residue
  4. stirringthe mixture was stirred at room temperature for 15 min
  5. concentrationAfter concentration
  6. customthe residue was purified by silica gel chromatography (NH, hexane/ethyl acetate)
  7. customthe obtained crystals were recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-ec9d2b4d22bf44989f28fa6b616c3649
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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