Water → HCID 11553138, compound

HRID 1092269Notes

Reaction equation

HRID 1092269 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH2:14][C:15]1[S:19][CH:18]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=2)[CH:16]=1)[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O1CCCC1.CO.O>C(O)(=O)C>[CH3:3][N:4]([CH2:14][C:15]1[S:19][CH:18]=[C:17]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:24][CH:25]=2)[CH:16]=1)[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 66591074HCID 66591074, compound

Product 1

HCID 11553138HCID 11553138, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

100 mg (2.5 mmol, 4 eq) of sodium hydroxide are added to a solution of 245 mg (0.57 mmol, 1 eq) of ethyl 3-(4-{5-[(methyloctanoylamino)methyl]thiophen-3-yl}phenyl)propanoate in 4 mL of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for two 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 (90/10 dichloromethane/methanol). The oil obtained is crystallized from pentane. 85 mg of 3-(4-{5-[(methyloctanoylamino)methyl]thiophen-3-yl}phenyl)propanoic acid are obtained. Yield=37%.

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 (90/10 dichloromethane/methanol)
  5. customThe oil obtained
  6. customis crystallized from pentane

Sources & evidence

ORD record
ord-914b23790e2c4c5296a44afc4d1c0d57
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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