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

HRID 1765874Notes

Reaction equation

HRID 1765874 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:23]=[C:22]([CH:24]3[CH2:26][CH2:25]3)[C:21]3[CH:20]([N:27]([CH:29]4[CH2:31][CH2:30]4)[CH3:28])[CH2:19][CH2:18][C:17]([CH3:33])([CH3:32])[C:16]=3[CH:15]=2)=[CH:8][CH:7]=1)[CH3:5].[OH-].[Li+].[Cl-].[NH4+]>CO.O1CCCC1>[CH:24]1([C:22]2[C:21]3[CH:20]([N:27]([CH:29]4[CH2:30][CH2:31]4)[CH3:28])[CH2:19][CH2:18][C:17]([CH3:32])([CH3:33])[C:16]=3[CH:15]=[C:14]([C:13]#[C:12][C:9]3[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:3]([OH:34])=[O:2])=[CH:11][CH:10]=3)[CH:23]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 69076829HCID 69076829, compound2×

Product 1

HCID 112592692-{4-[4-Cyclopropyl-5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-propionic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{4-[4-cyclopropyl-5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-propionic acid methyl ester (Intermediate 165, 0.075 g, 0.16 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL) was treated with 2M lithium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at ambient temperature for 5 h. The reaction mixture was neutralized with ammonium chloride and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid (0.07 g, 96%).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e2b11f03bef047588302d9ac895ef197
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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