Lithium Hydroxide → HCID 23042661, compound

HRID 2165973Notes

Reaction equation

HRID 2165973 reaction equation
C[O:2][C:3](=[O:6])[CH2:4][NH2:5].[CH2:7]([O:14][C:15]1[C:16]([N+:25]([O-:27])=[O:26])=[C:17]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:18]([NH2:20])=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Li+]>CO>[NH2:5][CH2:4][C:3]([OH:6])=[O:2].[N+:25]([C:16]1[C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:23]([CH3:24])[CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19])([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23042653HCID 23042653, compound

Product 1

HCID 23042661HCID 23042661, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7.5 g (21 mmol) 4a in 250 ml methanol were added 100 ml of 1N lithium hydroxide and the mixture was allowed to stir at room temperature for 2 hours. The methanol was removed under reduced pressure followed by dilution with 150 ml water and slow acidification with 6N hydrochloric acid to pH 1. The product was removed by filtration and washed with 0.1N hydrochloric acid and ether followed by vacuum drying. The 6.8 g of crude product were digested in 250 ml boiling chloroform then allowed to stand at 5° C. overnight. Filtration followed by vacuum drying gave 6.5 g (90%) 4b as marble white crystals: NMR (DMSO-d6) δ 12.7 (s.1H), 9.12 (t, 1H, j=6 Hz), 7.59 (s, 2H), 7.41 (s,5H), 4.94 (s, 2H), 3.86 (d, 2H, j=6 Hz), 2.37 (s, 3H).

Workup

  1. customThe methanol was removed under reduced pressure
  2. customThe product was removed by filtration
  3. washwashed with 0.1N hydrochloric acid and ether
  4. customdrying
  5. waitto stand at 5° C. overnight
  6. filtrationFiltration
  7. customdrying

Sources & evidence

ORD record
ord-44f003b1c7b845c7b1ff7998867cb794
Source dataset
uspto-grants-1990_07
Patent number
US04942227

Reaction notes

Loading…