Water → 5-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

HRID 1348959Notes

Reaction equation

HRID 1348959 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](=[O:31])[NH:8][C:9]=1[CH2:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[CH:14][CH:13]=1)=[O:4].C1COCC1.CO.[OH2:39].OOS([O-])=O.[K+].C([O-])(O)=O.[Na+].[OH2:51]>>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](=[O:31])[NH:8][C:9]=1[CH2:10][S:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[CH:14][CH:13]=1)(=[O:51])=[O:39])=[O:4]

Participants

6

Reactant 5

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21892291Methanol tetrahydrofuran waterHCID 23707502Potassium hydroxy sulfiteHCID 694323295-[4-(2-methyl-quinolin-4-ylmethoxy)-phenylsulfanylmethyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

Product 1

HCID 112021715-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl esterYield 85%

Conditions

Temperature
0 °C

Procedure

To a solution of 4e (11 mg, 0.025 mmol) in 5 mL of a mixture of THF:MeOH:H2O (2:1:2) was added a solution of Oxone® (31 mg, 0.05 mmol) in H2O, buffered with NaHCO3 (0.05 mmol). The solution was stirred at 0° C. for 1 h and filtered. The filtrate was concentrated and purified by flash column chromatography to provide 5-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester 4f (10 mg, 85%). MS (ESI+) (M+1)=468.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-0d5e9300d614468abbd0407f62de4825
Source dataset
uspto-grants-2007_05
Patent number
US07211671B2

Reaction notes

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