Sodium hydride → ({2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl ester

HRID 1265332

Reaction equation

HRID 1265332 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:22]1[CH:30]=[C:29]([O:31][CH3:32])[C:25]2[O:26][CH2:27][O:28][C:24]=2[CH:23]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])(=[O:13])=[O:12].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36]>O1CCCC1>[CH3:38][O:37][C:35](=[O:36])[CH2:34][N:14]([S:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:4]([OH:3])[C:22]1[CH:30]=[C:29]([O:31][CH3:32])[C:25]2[O:26][CH2:27][O:28][C:24]=2[CH:23]=1)(=[O:12])=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 186155802-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamide

Product 1

HCID 22965597({2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl esterYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sixty percent sodium hydride suspension in oil (0.422 g, 10.55 mmol) was washed with tetrahydrofuran and was added to tetrahydrofuran (175 mL). To this was added 2-[hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamide (4.1 g, 9.59 mmol). After stirring for 30 minutes, methyl bromoacetate (1.09 mL, 11.5 mmol) was added followed by stirring at reflux for 18 hours. The mixture was evaporated to an oil in vacuo, and the residue was resuspended in ethyl ether, washed with 1N citric and brine. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to a solid. The material was chromatographed on 300 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo from ethyl ether giving a solid, 4.29 g, 89.5% yield. NMR spectra and elemental analysis were consistent with the structure.

Workup

  1. stirringby stirring
  2. temperatureat reflux for 18 hours
  3. customThe mixture was evaporated to an oil in vacuo
  4. washwashed with 1N citric
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to a solid
  8. customThe material was chromatographed on 300 g silica gel
  9. washeluted with a mixture of ethyl acetate and hexane (35:65)
  10. concentrationThe appropriate fractions were concentrated in vacuo from ethyl ether giving a solid, 4.29 g, 89.5% yield

Sources & evidence

ORD record
ord-d4ae79b639364b7c95cf8c3f88f6d52e
Source dataset
uspto-grants-2003_04
Patent number
US06545150B2

Linked notes

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