Water → HCID 67147907, compound

HRID 910328Notes

Reaction equation

HRID 910328 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:9]([O:11][C@@H:12]([CH2:17][C:18]1[CH:19]=[N:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([CH3:43])[C:31](OC3C=CC([N+]([O-])=O)=CC=3)=[O:32])[CH:25]=2)=[CH:22][CH:23]=1)[C:13]([O:15][CH3:16])=[O:14])[CH3:10].O>CN(C)C=O>[CH2:9]([O:11][C@@H:12]([CH2:17][C:18]1[CH:19]=[N:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([CH3:43])[C:31]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:32])[CH:25]=2)=[CH:22][CH:23]=1)[C:13]([O:15][CH3:16])=[O:14])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 81271-HeptanamineHCID 67147910HCID 67147910, compound

Product 1

HCID 67147907HCID 67147907, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

70 μl (0.45 mmol) of heptylamine are added to a solution of 110 mg (0.25 mmol) of methyl 2(S)-ethoxy-3-(6-{3-[methyl(4-nitrophenoxycarbonyl)amino]phenyl}pyrid-3-yl)propanoate in 3 ml of dimethylformamide. The reaction medium is heated at 80° C. for 3 hours. After addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 6/4 and then 5/5 heptane/ethyl acetate mixture. 50 mg (50%) of methyl 2(S)-ethoxy-3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}propanoate are obtained.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by thin-layer chromatography on silica
  7. washeluted with a 6/4

Sources & evidence

ORD record
ord-fa1277d160394c54a1de0210e7e064a1
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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