Hydrochloric Acid → HCID 9869528, compound

HRID 2268114Notes

Reaction equation

HRID 2268114 reaction equation
C([O:3][C:4](=[O:32])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([S:23]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)(=[O:25])=[O:24])[CH:17]=2)=[C:10]([Cl:31])[CH:9]=1)=[O:6])C.Cl>O.CO.[OH-].[K+]>[Cl:14][C:12]1[CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]([OH:32])=[O:3])[CH:9]=[C:10]([Cl:31])[C:11]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([S:23]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)(=[O:25])=[O:24])[CH:17]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15541444HCID 15541444, compound

Product 1

HCID 9869528HCID 9869528, compound

Reagents, catalysts & solvents 3

HCID 14797Potassium HydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-{3,5-dichloro-4-[4-hydroxy-3-(pyrrolidine-1-sulfonyl)-phenoxy]-phenyl}-oxamic acid ethyl ester (10 mg, 0.02 mmol) in a mixture of H2O (0.5 mL) and MeOH (0.5 mL) was added 2 drops of 3N KOH. The reaction mixture was stirred at RT for 2 h, acidified with 1N HCl and extracted with EtOAc (4×5 mL). The combined organic extracts were dried and concentrated to afford the title compound as an off-white solid. NMR (400 MHz, CD3OD) d 7.96 (s, 2H), 7.02-7.06 (m, 2H), 6.95-6.98 (d, 1H), 3.28-3.31 (m, 4H), 1.78-1.81 (m, 4H). MS Calc.: 474.3 Found: 473.1 (M−1).

Workup

  1. extractionextracted with EtOAc (4×5 mL)
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ac6da5277cd04260b12f586274c72719
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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