Potassium Carbonate → HCID 70130702, compound

HRID 964446Notes

Reaction equation

HRID 964446 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:13]=2[O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:12]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:13]=2[O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86752384HCID 86752384, compound

Product 1

HCID 70130702HCID 70130702, compoundYield 71.5%

Reagents, catalysts & solvents 1

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

Procedure

4-[2-[[(4-Acetylphenyl)amino]methyl]-6-methoxy-phenoxy]butanoic acid, ethyl ester (250 mg, 0.65 mmol) is dissolved in 5 mL of methanol/water (3:2) and treated with 313 mg (2.27 mmol) of potassium carbonate according to the procedure described for Example 4 to give 166 mg (71%) of 4-[2-[[(4-acetylphenyl)amino]methyl]-6-methoxy-phenoxy]butanoic acid as a red colored solid: m.p. 85°-95° C.; The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (KBr) 3400, 1720, 1630, 1580 cm-1 ; MS (CI) m/e calculated for C20H23 O5NNa: 380.1473, found 380.1482; 358 (M+H), 233, 223, 221, 136.

Sources & evidence

ORD record
ord-5e16d127898a492493e34c78c98a7764
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

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