Hydrochloric Acid → HCID 54326757, compound

HRID 1637112Notes

Reaction equation

HRID 1637112 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH:5]([C:20]#[C:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([O:30][CH3:31])=[O:29])[CH:23]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1.[OH-].[Na+].Cl>CO.O>[C:28]([C:24]1[CH:23]=[C:22]([C:21]#[C:20][CH:5]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:7]=2)[CH2:4][C:3]([OH:32])=[O:2])[CH:27]=[CH:26][CH:25]=1)([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54515943HCID 54515943, compound

Product 1

HCID 54326757HCID 54326757, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (+/-)-methyl-3-(3-carbomethoxyphenyl)ethynyl-3-(3-cyclopentyloxy-4-methoxyphenyl)propionate (0.14 g, 0.32 mmol) in 5:2 methanol/water was added NaOH (0.01 g, 0.32 mmol). After 24 h, 3N HCl was added, the methanol was evaporated and the aqueous residue was extracted twice with CH2Cl2 and was evaporated. Purification by flash chromatography (silica gel, 5% CH3OH/CHCl3) provided the title compound as a yellow oil (0.02 g, 13%). Anal (C25H26O6 ·0.25H20) calcd: C, 70.32; H, 6.26. found: C, 70A6; H, 6.45.

Workup

  1. customthe methanol was evaporated
  2. extractionthe aqueous residue was extracted twice with CH2Cl2
  3. customwas evaporated
  4. customPurification by flash chromatography (silica gel, 5% CH3OH/CHCl3)

Sources & evidence

ORD record
ord-46e56a476eea43a3800582b6cbfd33cc
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

Loading…