Water → HCID 21829888, compound

HRID 1600535Notes

Reaction equation

HRID 1600535 reaction equation
[CH3:1][C:2]([N:7]1[C:12](=[O:13])[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:10]([CH3:20])[O:9][CH2:8]1)([CH3:6])[C:3]([OH:5])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:33]([NH2:36])([CH3:35])[CH3:34].O>O1CCCC1>[CH:33]([NH:36][C:3](=[O:5])[C:2]([CH3:1])([N:7]1[C:12](=[O:13])[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:10]([CH3:20])[O:9][CH2:8]1)[CH3:6])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 221182822-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionic acid

Product 1

HCID 21829888HCID 21829888, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionic acid (0.83 g) in 6 ml of tetrahydrofuran (THF) was added carbonyldiimidazole (0.59 g). After stirring at room temperature for 30 min., isopropylamine (0.23 g) was added and the reaction mixture was stirred at 60° C. for 5 h. Then it was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column to get the captioned compound (0.38 g).

Workup

  1. stirringthe reaction mixture was stirred at 60° C. for 5 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-586f92a24aa944c2b8cd779832874951
Source dataset
uspto-grants-1999_11
Patent number
US05977025

Reaction notes

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