Hydrogen chloride-ethyl acetate → N-((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide

HRID 2277161Notes

Reaction equation

HRID 2277161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=O)[O:28]C(C)(C)C)[CH3:25])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.Cl.[C:35](OCC)(=O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:28])[CH3:35])[CH3:25])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86731213tert-butyl ((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate

Product 1

HCID 86731214N-((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide

Procedure

To tert-butyl ((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate (1.09 g) was added 4 M hydrogen chloride/ethyl acetate (10 mL), and the mixture was stirred at room temperature for 10 min, and concentrated. To the residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (640 mg). 1H NMR (300 MHz, CDCl3) δ 0.39-0.49 (2H, m), 0.63-0.75 (2H, m), 1.28-1.43 (4H, m), 2.02 (3H, s), 3.95-4.09 (4H, m), 4.36-4.50 (1H, m), 5.74 (1H, d, J=8.3 Hz), 6.95 (1H, dd, J=8.9, 2.5 Hz), 7.00 (1H, d, J=8.7 Hz), 7.11 (1H, d, J=2.3 Hz), 7.60 (1H, d, J=8.7 Hz), 8.04 (1H, dd, J=8.7, 1.9 Hz), 8.22 (1H, d, J=1.9 Hz).

Workup

  1. concentrationconcentrated
  2. additionTo the residue were added pyridine (10 mL) and acetic anhydride (10 mL)
  3. stirringthe mixture was stirred at room temperature for 15 min
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d36cc0c3a76244a0993aa92752267120
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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