Lithium Hydroxide → HCID 44375597, compound

HRID 2121256Notes

Reaction equation

HRID 2121256 reaction equation
C[N:2]([C:11](=[O:33])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:14][C:13]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])[C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][S:6][CH3:7].[Li+].[OH-]>CO>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:19]#[C:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]([NH:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][S:6][CH3:7])=[O:33])=[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH:14]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69892721HCID 69892721, compound

Product 1

HCID 44375597HCID 44375597, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl N-[4-(2-pyrid-3-ylethyn-1-yl)-2-(2-methylphenyl)benzoyl]methionine (43 mg, 0.09 mmol) was dissolved in MeOH (2 mL) and treated with excess 1 M LiOH. After 18 h at room temperature, the reaction was evaporated, and partitioned between ether and water. The aqueous layer was acidified with 1 M HCl and extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4, and evaporated to provide 35 mg of the title compound. MS m/e 445 (M+H)+. 1H NMR (CDCl3, 300 MHz) 1.62 (m, 1H), 1.96 (m, 1H), 2.1 (m, 8H), 4.62 (m, 1H), 6.02 (m, 1H), 7.37 (m, 6H), 7.63 (m, 1H), 7.88 (m, 1H), 7.99 (m, 1H), 8.59 (m, 1H), 8.79 (m, 1H).

Workup

  1. customthe reaction was evaporated
  2. custompartitioned between ether and water
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-4021ac269d824931b0fc6b82649c0728
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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