Hydrochloric Acid → N-Cyclohexyl-3-(3-(oxazol-5-yl)phenethoxy)-N-(2-oxoethyl)propanamide

HRID 909909Notes

Reaction equation

HRID 909909 reaction equation
[CH:1]1([N:7]([CH2:26][CH:27](OC)[O:28]C)[C:8](=[O:25])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CC(C)=O>[CH:1]1([N:7]([CH2:26][CH:27]=[O:28])[C:8](=[O:25])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59290488N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(oxazol-5-yl)phenethoxy)propanamide

Product 1

HCID 59290455N-Cyclohexyl-3-(3-(oxazol-5-yl)phenethoxy)-N-(2-oxoethyl)propanamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of N-cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(oxazol-5-yl)phenethoxy)propanamide [Example 10, Step iii)] (660 mg) in acetone (30 mL) was added 2M hydrochloric acid (10 mL). The mixture was stirred for 6 h before the solvents were removed followed by the addition of saturated sodium hydrogen carbonate until basic. The mixture was extracted three times with ethyl acetate, and the pooled organic fractions were washed once with brine, dried over sodium sulphate, filtered and evaporated to afford the sub-titled compound (525 mg). This material was used in the next step directly.

Workup

  1. customwere removed
  2. additionfollowed by the addition of saturated sodium hydrogen carbonate until basic
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. washthe pooled organic fractions were washed once with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9c38f9c3d2e44b77bbdded6f82e442e6
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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