Lithium Hydroxide → HCID 59856230, compound

HRID 1869914Notes

Reaction equation

HRID 1869914 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[CH:14]([N:16]([CH:18]3[CH2:20][CH2:19]3)[CH3:17])[CH2:13][CH2:12][C:11]([CH3:22])([CH3:21])[C:10]=2[CH:9]=[C:8]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32]([O:34]C)=[O:33])=[CH:27][CH:26]=2)[CH:7]=1)=[O:5])[CH3:2].[OH-].[Li+]>C(O)C.O1CCCC1.O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[CH:14]([N:16]([CH:18]3[CH2:19][CH2:20]3)[CH3:17])[CH2:13][CH2:12][C:11]([CH3:22])([CH3:21])[C:10]=2[CH:9]=[C:8]([C:23]#[C:24][C:25]2[CH:26]=[CH:27][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:29][CH:30]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 69072587HCID 69072587, compound2×

Product 1

HCID 59856230HCID 59856230, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-(cyclopropyl-methyl-amino)-3-(4-methoxycarbonylmethyl-phenylethynyl)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid ethyl ester (Intermediate 78, 0.09 g, 0.19 mmol) in ethanol (2 mL), tetrahydrofuran (3 mL) and water (1.5 mL) was treated with lithium hydroxide (0.11 g, 2.62 mmol) and the resulting reaction mixture was stirred at ambient temperature for 2 h. The volatiles were evaporated in vacuo to a residue that was 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 white solid (0.085 g, 94%).

Workup

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

Sources & evidence

ORD record
ord-243b1a967fee46fe9c494cfd77860214
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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