Sodium Hydroxide → HCID 22467199, compound

HRID 1934606Notes

Reaction equation

HRID 1934606 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31](/[CH:35]=[CH:36]/[C:37]([O:39]CC)=[O:38])=[CH:32][CH:33]=4)[N:28]([CH3:42])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Na+]>O1CCCC1.CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31](/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38])=[CH:32][CH:33]=4)[N:28]([CH3:42])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:22]=3)(=[O:15])=[O:16])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18362635HCID 18362635, compound

Product 1

HCID 22467199HCID 22467199, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (E)-3-(3-1-(1,3-benzodioxol-5-yl)-2-[(4-isopropylphenyl)sulfonamido]-2-oxoethyl-1-methyl-1H-6-indolyl)-2-propenoate (the product of Example 57, 120 mg, 0.2 mmol) was dissolved in a 1:1 mixture of tetrahydrofuran and methanol (5 ml). Sodium hydroxide solution (0.6 ml of 1N NaOH) was added and the mixture was heated to reflux with stirring. After 3 h the solvent was removed in vacuo and the product was extracted from 1N hydrochloric acid (50 ml) with ethyl acetate (2×50 ml). The organic layers were dried (MgSO4) and concentrated. Purification by flash column chromatography (gradient elution from 100% dichloromethane to 90% dichloromethane/10% methanol/1% acetic acid) gave the product as a pale green foam (90 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customAfter 3 h the solvent was removed in vacuo
  4. extractionthe product was extracted from 1N hydrochloric acid (50 ml) with ethyl acetate (2×50 ml)
  5. dry with materialThe organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customPurification
  8. washby flash column chromatography (gradient elution from 100% dichloromethane to 90% dichloromethane/10% methanol/1% acetic acid)

Sources & evidence

ORD record
ord-fcb97309ac3748128038311efdc92c10
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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