Sodium Hydroxide → 2-[4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-pent-4-enoic acid

HRID 23584Notes

Reaction equation

HRID 23584 reaction equation
C([O:8][C:9](=[O:33])[CH:10]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:15]=1[S:24]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)(=[O:26])=[O:25])[CH2:11][CH:12]=[CH2:13])C1C=CC=CC=1.[OH-].[Na+]>CO.O>[CH3:23][O:22][C:17]1[C:18]([O:20][CH3:21])=[CH:19][C:14]([CH:10]([CH2:11][CH:12]=[CH2:13])[C:9]([OH:33])=[O:8])=[C:15]([S:24]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)(=[O:26])=[O:25])[CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 697313012-[4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-pent-4-enoic acid benzyl ester

Product 1

HCID 225732182-[4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-pent-4-enoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture 2-[4,5-dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-pent-4-enoic acid benzyl ester (3.25 g, 6.83 mmol) in methanol (28 cm3) under an atmosphere of dry nitrogen was added sodium hydroxide (820 mg, 20.5 mmol) dissolved in water (7 cm3). The mixture completely dissolved while stirring at ambient temperature for 20 hours. The volatile fractions were removed in vacuo and water (30 cm3) was added to the mixture. The aqueous mixture acidified with 6N HCl to pH 1.0 and was extracted with dichloromethane (3×30 cm3). The combined extracts were washed with brine (30 cm3), dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to a crude golden oil. The oil was triturated in Et2O (30 cm3), vacuum filtered, washed with Et2O (2×10 cm3) and vacuum dried to constant weight to afford the title compound as (2.30 g, 87.54%) with a positive ion ESI (M+H)+386.2.

Workup

  1. dissolutionThe mixture completely dissolved
  2. customThe volatile fractions were removed in vacuo and water (30 cm3)
  3. additionwas added to the mixture
  4. extractionwas extracted with dichloromethane (3×30 cm3)
  5. washThe combined extracts were washed with brine (30 cm3)
  6. dry with materialdried over sodium sulfate, vacuum
  7. filtrationfiltered
  8. customthe filtrate volatile fractions removed in vacuo to a crude golden oil
  9. customThe oil was triturated in Et2O (30 cm3)
  10. filtrationvacuum filtered
  11. washwashed with Et2O (2×10 cm3) and vacuum
  12. customdried to constant weight

Sources & evidence

ORD record
ord-7caf2594e6bf4d3d8d2fcf66f8ea9bb5
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

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