Sodium Hydroxide → HCID 19792778, compound

HRID 1655625Notes

Reaction equation

HRID 1655625 reaction equation
C[O:2][C:3]([N:5]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][C:7](=[O:24])[NH:6]1)=[O:4].[OH-].[Na+]>CO>[CH:19]1([O:18][C:12]2[CH:11]=[C:10]([CH:9]3[N:5]([C:3]([OH:4])=[O:2])[NH:6][C:7](=[O:24])[CH2:8]3)[CH:15]=[CH:14][C:13]=2[O:16][CH3:17])[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53690363HCID 53690363, compound

Product 1

HCID 19792778HCID 19792778, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-[3-(cyclopentyloxy)-4-methoxyphenyl]-3-oxo-l-pyrazolidinecarboxylic acid methyl ester (0.696 g, 2 mmol) in methanol (4 ml) is mixed with 2.5 N sodium hydroxide solution (1.2 ml, 3 mmol). The reaction mixture is kept at 40° overnight. The solvent is removed, and the residue partitioned between ethyl acetate/water, dried and the solvent evaporated. Residue (0.7 g) is allowed to crystallize over ethyl acetate/ether to yield solid (0.29 g) m.p. 137-139°. A crystallization from ethyl acetate/ether gives analytical sample m.p. 136 NMR (Me2SO-d6); δ 9.38 (1H, broad, NH), 7.02 (1H, d, arom), 6.89 (2H, m, arom), 4.75 (1H, m, carbinolic), 4.27 (1H, q, benzylic), 3.72 (3H, s, 0--CH3), 3.60 (1H, d, --CHCO), 3.37 (1H, d, --CHCO), 3.04 (1H, q, --CHCO), 2.25 (1H, q, --CHCO), 1.88 (2H, m, cyclopentyl --CH), 1.70 (4H, m, cyclopentyl --CH), 1.56 (2H, m, cyclopentyl --CH), IR (KBr), 3210, 2940, 2450, 1710, 1630, 1510 cm-1.

Workup

  1. customThe solvent is removed
  2. customthe residue partitioned between ethyl acetate/water
  3. customdried
  4. customthe solvent evaporated
  5. customto crystallize over ethyl acetate/ether

Sources & evidence

ORD record
ord-084c0ce34a0848499862babbd4a74e0f
Source dataset
uspto-grants-1993_10
Patent number
US05250700

Reaction notes

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