Sodium Hydroxide → 2-{4-[5-(Cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-2-methyl-propionic acid

HRID 1870017Notes

Reaction equation

HRID 1870017 reaction equation
C[O:2][C:3](=[O:32])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:22]3[CH:21]([N:25]([CH:27]4[CH2:29][CH2:28]4)[CH3:26])[CH2:20][CH2:19][C:18]([CH3:31])([CH3:30])[C:17]=3[CH:16]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+]>CO.O1CCCC1>[CH:27]1([N:25]([CH3:26])[CH:21]2[CH2:20][CH2:19][C:18]([CH3:30])([CH3:31])[C:17]3[CH:16]=[C:15]([C:14]#[C:13][C:10]4[CH:9]=[CH:8][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:32])=[O:2])=[CH:12][CH:11]=4)[CH:24]=[CH:23][C:22]2=3)[CH2:28][CH2:29]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 690695532-{4-[5-(Cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-2-methyl-propionic acid methyl ester2×

Product 1

HCID 113959052-{4-[5-(Cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-2-methyl-propionic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{4-[5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-2-methyl-propionic acid methyl ester (Intermediate 170, 0.08 g, 0.19 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) was treated with a 2M solution of sodium hydroxide (2 mL, 4 mmol) and the resulting reaction mixture was refluxed overnight. The volatiles were evaporated in vacuo and the residue was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product (0.07 g, ˜100%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customThe volatiles were evaporated in vacuo
  4. additionthe residue was diluted with saturated aqueous ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-1260c2db1c064754b8e775abc9e6ef4a
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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