Water → HCID 11646949, compound

HRID 1092280Notes

Reaction equation

HRID 1092280 reaction equation
[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:33])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[N:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O1CCCC1.CO.O>C(O)(=O)C>[CH2:3]([NH:10][C:11](=[O:33])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[N:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 66591351HCID 66591351, compound

Product 1

HCID 11646949HCID 11646949, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

200 mg (5 mmol, 4 eq) of sodium hydroxide are added to a solution of 488 mg (1.14 mmol, 1 eq) of ethyl 3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}propanoate in 6 mL of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for 3 hours at room temperature. The reaction is stopped by adding 20 ml of water and 3 ml of acetic acid and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 to 50/50 heptane/ethyl acetate). The oil obtained is crystallized from pentane. 442 mg of 3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}propanoic acid are obtained. Yield=94%. m.p.=118° C.

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 to 50/50 heptane/ethyl acetate)
  5. customThe oil obtained
  6. customis crystallized from pentane

Sources & evidence

ORD record
ord-4c1a1c3da42f4207a46499e0d3930c0f
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

Loading…