Ethylamine → HCID 68549753, compound

HRID 2242564Notes

Reaction equation

HRID 2242564 reaction equation
[OH:1][CH:2]([CH:8]([N:15]([CH3:23])[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5]CC)=O.[CH2:24]([NH2:26])[CH3:25]>>[CH2:24]([NH:26][C:3](=[O:5])[CH:2]([OH:1])[CH:8]([N:15]([CH3:23])[C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:25]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 86619546HCID 86619546, compound

Product 1

HCID 68549753HCID 68549753, compoundYield 57%

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl (2RS,3RS)-2-hydroxy-3-[methyl(4-methylphenyl)amino]-3-phenylpropanoate (Example 12, step 1, 948 mg, 3.03 mmol) and methanolic ethylamine solution (2.0 M in methanol, 25 mL) was stirred at 120° C. in a sealed tube for 48 hours. After cooling, all volatiles were removed under reduced pressure. The crude product was purified by flash column chromatography (silica gel, 0-15% ethyl acetate/hexane) and recrystallized (warm chloroform/hexane/−25° C.) to yield 537 mg (57%) of (2RS,3RS)-N-ethyl-2-hydroxy-3-[methyl(4-methylphenyl)amino]-3-phenylpropanamide as a white solid. MS (ESI) m/z 313 ([M+H]+); HRMS: calculated for C19H24N2O2+H, 313.1911; found (ESI, [M+H]+), 313.1908.

Workup

  1. temperatureAfter cooling
  2. customall volatiles were removed under reduced pressure
  3. customThe crude product was purified by flash column chromatography (silica gel, 0-15% ethyl acetate/hexane)
  4. customrecrystallized
  5. temperature(warm chloroform/hexane/−25° C.)

Sources & evidence

ORD record
ord-325ce4bf99f84af8b560e61b4c852339
Source dataset
uspto-grants-2010_03
Patent number
US07671238B2

Reaction notes

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