Sodium Hydroxide → 2-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-propionic acid

HRID 2377327Notes

Reaction equation

HRID 2377327 reaction equation
C[O:2][C:3](=[O:34])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([CH2:24][N:25]([CH:27]4[CH2:29][CH2:28]4)[CH3:26])[CH:23]=2)[O:20][C:19]([CH3:31])([CH3:30])[CH2:18][C:17]3([CH3:33])[CH3:32])=[CH:8][CH:7]=1)[CH3:5].[OH-].[Na+]>CO.O1CCCC1>[CH:27]1([N:25]([CH2:24][C:22]2[CH:23]=[C:14]([C:13]#[C:12][C:9]3[CH:10]=[CH:11][C:6]([CH:4]([CH3:5])[C:3]([OH:34])=[O:2])=[CH:7][CH:8]=3)[CH:15]=[C:16]3[C:21]=2[O:20][C:19]([CH3:30])([CH3:31])[CH2:18][C:17]3([CH3:33])[CH3:32])[CH3:26])[CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 690760872-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-propionic acid methyl ester2×

Product 1

HCID 112361692-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-propionic acidYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-{8-[(cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-propionic acid methyl ester (Intermediate 14, 0.057 g, 0.12 mmol) in methanol (1 mL) and tetrahydrofuran (3 mL) was treated with a 1M solution of sodium hydroxide (0.3 mL, 0.3 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo to a residue that was washed with hexane, neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid (0.024 g, 45%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo to a residue that
  3. washwas washed with hexane
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-74a4d845d286424aa94c2b962d0abef3
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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