Methylamine → HCID 68547740, compound

HRID 2242562Notes

Reaction equation

HRID 2242562 reaction equation
[OH:1][CH:2]([CH:8]([N:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](OCC)=[O:4].[CH3:23][NH2:24]>>[OH:1][CH:2]([CH:8]([N:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([NH:24][CH3:23])=[O:4]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 12472783HCID 12472783, compound

Product 1

HCID 68547740HCID 68547740, compoundYield 99%

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl (2RS,3RS)-2-hydroxy-3-[methyl(phenyl)amino]-3-phenylpropanoate (Example 1, Step 1, 375 mg, 1.25 mmol) and ethanolic methylamine solution (33 weight % in absolute ethanol, 5 mL) was stirred at 80° C. in a sealed tube for 5 hours. After cooling, all volatiles were removed under reduced pressure. The resulting solid was recrystallized (warm chloroform/hexane/−25° C.) to yield 350 mg (99%) (2RS,3RS)-2-hydroxy-N-methyl-3-[methyl(phenyl)amino]-3-phenylpropanamide as white needles. MS (ESI) m/z 285 ([M+H]+); HRMS: calculated for C17H20N2O2+H, 285.1598; found (ESI, [M+H]+), 285.1592.

Workup

  1. temperatureAfter cooling
  2. customall volatiles were removed under reduced pressure
  3. customThe resulting solid was recrystallized
  4. temperature(warm chloroform/hexane/−25° C.)

Sources & evidence

ORD record
ord-af83a8d719f1494b82fa6c9807d4fd40
Source dataset
uspto-grants-2010_03
Patent number
US07671238B2

Reaction notes

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