Lithium Hydroxide → HCID 21107176, compound

HRID 2377454Notes

Reaction equation

HRID 2377454 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[C:21]([O:23][CH:24]([CH3:26])[CH3:25])[C:20]3[CH:19]([N:27]([CH:29]4[CH2:31][CH2:30]4)[CH3:28])[CH2:18][CH2:17][C:16]([CH3:33])([CH3:32])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Li+]>CO.O1CCCC1>[CH:29]1([N:27]([CH3:28])[CH:19]2[CH2:18][CH2:17][C:16]([CH3:33])([CH3:32])[C:15]3[CH:14]=[C:13]([C:12]#[C:11][C:8]4[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:34])=[O:2])=[CH:10][CH:9]=4)[CH:22]=[C:21]([O:23][CH:24]([CH3:25])[CH3:26])[C:20]2=3)[CH2:30][CH2:31]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57424256HCID 57424256, compound2×

Product 1

HCID 21107176HCID 21107176, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {4-[5-(cyclopropyl-methyl-amino)-4-isopropoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acetic acid methyl ester (Intermediate 129, 0.045 g, 0.098 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 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 a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% methanol in ethyl acetate as the eluent to afford the title product as a white solid (0.027 g, 61%).

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 to a residue that

Sources & evidence

ORD record
ord-157bb910bc884a99a39068c8af21e807
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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