Sodium Hydroxide → HCID 69781317, compound

HRID 1279011Notes

Reaction equation

HRID 1279011 reaction equation
[OH-].[Na+].[ClH:3].C[O:5][C:6](=[O:38])[CH:7]([NH:20][C:21](=[O:37])[CH2:22][NH:23][S:24]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)(=[O:26])=[O:25])[CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([NH2:19])=[N:14][CH:13]=[CH:12]2>O1CCOCC1.O>[ClH:3].[NH2:19][C:15]1[C:16]2[C:11](=[CH:10][C:9]([CH2:8][CH:7]([NH:20][C:21](=[O:37])[CH2:22][NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:6]([OH:38])=[O:5])=[CH:18][CH:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69781099HCID 69781099, compound

Product 1

HCID 69781317HCID 69781317, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.16 mL of aqueous 2N NaOH was added to a solution of 47 mg of 1k in 1.0 mL of dioxane and 0.5 mL water. After stirring at room temperature for one hour, the reaction mixture was made acidic (pH 2) and extracted with a mixture of n-butanol and dichloromethane. Evaporation of the organic solvents yielded 47 mg of acid 2a. 1H-NMR 200 MHz (CDCl3/CD3OD=3/1) δ: 3.20-3.65 (4H, m), 4.87 (1H, dd, J=7 Hz and J=5 Hz), 7.10 (1H, d, J=7 Hz), 7.41 (1H, d, J=7 Hz), 7.58-8.03 (8H, m), 8.29 (1H, d, 7 Hz), 8.41 (1H, d, 2 Hz)

Workup

  1. extractionextracted with a mixture of n-butanol and dichloromethane
  2. customEvaporation of the organic solvents

Sources & evidence

ORD record
ord-1e3b986e598e451ea39979640e440f13
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

Loading…