Sodium Hydroxide → HCID 57989587, compound

HRID 2059889Notes

Reaction equation

HRID 2059889 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][C@H:16]2[CH2:24][OH:25])(=[O:14])=[O:13])=[C:7]([CH3:26])[CH:6]=1.[C:27]([O:31][C:32](=[O:35])[CH2:33]Br)([CH3:30])([CH3:29])[CH3:28]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH3:26])[C:8]([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][C@H:16]2[CH2:24][O:25][CH2:33][C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:35])(=[O:13])=[O:14])=[C:9]([CH3:11])[CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 57989609(S)-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanol

Product 1

HCID 57989587HCID 57989587, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

35% sodium hydroxide solution (10 ml) was added to a cooled (0° C.) solution of (S)-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanol (3.3 mmol, 1.0 eq) and tetra-n-butylammonium chloride (1.1 mmol, 0.33 eq) in toluene (20 ml). tert-Butylbromoacetate (1.5 eq) was added slowly to this mixture and the mixture was stirred for 2 h at room temperature. The organic phase was separated off and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with water and saturated sodium chloride solution, dried over Na2SO4 and concentrated to small volume under vacuum. The crude product was processed by column chromatography. Yield: 50%

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. washThe combined organic phases were washed with water and saturated sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-b61b749c70354dab931c850efd0d29cf
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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