Sodium Hydroxide → HCID 69781317, compound

HRID 2304235Notes

Reaction equation

HRID 2304235 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/CD3 OD=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-04d9f1c7685c478490fd7d3e9c1b19ce
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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