Ammonia → HCID 12472766, compound

HRID 2242559Notes

Reaction equation

HRID 2242559 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].[NH3:23]>>[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]([NH2:23])=[O:4]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 12472783HCID 12472783, compound

Product 1

HCID 12472766HCID 12472766, compoundYield 54%

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl (2RS,3RS)-2-hydroxy-3-[methyl(phenyl)amino]-3-phenylpropanoate (1.20 g, 4.00 mmol) and methanolic ammonia solution (7 N, 20 mL) was stirred at 100° C. in a sealed tube for 5 hours. After cooling, all volatiles were removed under reduced pressure. The resulting yellow oil was purified via silica gel chromatography (15-30% isopropanol/hexane) and recrystallized (warm ethyl acetate/hexane/−25° C.) to yield 582 mg (54%) of (2RS,3RS)-2-hydroxy-3-[methyl(phenyl)amino]-3-phenylpropanamide as white needles. MS (ESI) m/z 268.9 ([M−H]−); HRMS: calculated for C16H18N2O2+H, 271.1447; found (ESI, [M+H]+), 271.1458.

Workup

  1. temperatureAfter cooling
  2. customall volatiles were removed under reduced pressure
  3. customThe resulting yellow oil was purified via silica gel chromatography (15-30% isopropanol/hexane)
  4. customrecrystallized
  5. temperature(warm ethyl acetate/hexane/−25° C.)

Sources & evidence

ORD record
ord-1b6bd25cb7674f5982223226f4c76e9a
Source dataset
uspto-grants-2010_03
Patent number
US07671238B2

Reaction notes

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