Water → [4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-acetic acid benzyl ester

HRID 23582Notes

Reaction equation

HRID 23582 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[S:21](Cl)(=[O:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.O>O1CCCC1>[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[S:21]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)(=[O:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 86594678HCID 86594678, compound

Product 1

HCID 69732356[4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-acetic acid benzyl esterYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of (2-chlorosulfonyl-4,5-dimethoxy-phenyl)-acetic acid benzyl ester (15.0 g, 39.0 mmol) in anhydrous tetrahydrofuran (45 cm3) cooled to 0° C. in an ice bath under an atmosphere of dry nitrogen was added triethylamine (6.00 cm3, 43 mmol). The mixture was stirred 2 minutes and morpholine (3.75 cm3, 43 mmol) was added dropwise to form a solid mass. To efficiently stir the mixture additional anhydrous tetrahydrofuran (145 cm3) was added and the mixture was warmed to ambient temperature over 20 hours. Water was added to the mixture and extracted with ethyl acetate (2×100 cm3). The combined ethyl acetate extracts were dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to afford a crude tan solid. The crude solid was recrystallized from toluene (150 cm3) to afford the title compound as tan crystals (10.2 g, 60.2%) with a positive ion ESI (M+H)+436.2.

Workup

  1. customto form a solid mass
  2. additionwas added
  3. temperaturethe mixture was warmed to ambient temperature over 20 hours
  4. extractionextracted with ethyl acetate (2×100 cm3)
  5. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate, vacuum
  6. filtrationfiltered
  7. customthe filtrate volatile fractions removed in vacuo
  8. customto afford a crude tan solid
  9. customThe crude solid was recrystallized from toluene (150 cm3)

Sources & evidence

ORD record
ord-1d10b31161ba47608dd5f6a1f763fcbb
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

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