Potassium Hydroxide → HCID 21085790, compound

HRID 348823Notes

Reaction equation

HRID 348823 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]#[CH:18])[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3].[OH-].[K+]>CO.O.C(Cl)(Cl)Cl>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]#[CH:18])[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:20][CH3:21]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 21086178Methyl 3-[(dipropylamino)carbonyl]-5-ethynylbenzoate

Product 1

HCID 21085790HCID 21085790, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred mixture of the protected methyl 3-[(dipropylamino)carbonyl]-5-ethynylbenzoate (XXXII, Step 1, 185.3 mg, 0.49 mmol) in methanol (2.5 mL) is added a mixture of potassium hydroxide (2.9 mL of a 1 M mixture in water, 2.9 mmol). The reaction mixture is stirred for 4 hours diluted with chloroform (40 mL), the phases are separated and the organic phase is concentrated under reduced pressure to give 3-[(dipropylamino)carbonyl]-5-ethynylbenzoic acid, NMR (300 MHz, CDCl3): δ 8.22, 8.05, 7.71, 3.48, 3.17, 3.16, 1.71, 1.55, 1.00 and 0.78.

Workup

  1. additionis added
  2. customthe phases are separated
  3. concentrationthe organic phase is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2e92fb8afaa464badd5547341198f1e
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

Loading…