Sodium Hydroxide → HCID 59591076, compound

HRID 2383323Notes

Reaction equation

HRID 2383323 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[C:20]([CH3:44])=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH:25]([CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[N:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:23][CH2:22]4)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[C:20]([CH3:44])=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH:25]([CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[N:24]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH2:23][CH2:22]4)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59591097HCID 59591097, compound

Product 1

HCID 59591076HCID 59591076, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (1 ml) and 2M sodium hydroxide (1 ml) were added to 1,1-dimethylethyl 6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 30; 100 mg, 0.17 mmol) and the mixture stirred at room temperature for 3 hours. The ethanol was evaporated and the residue acidified with glacial acetic acid. The mixture was extracted with ethyl acetate (2×2 ml). The combined extracts were dried and evaporated. The residue was triturated with iso-hexane to give the title compound (51 mg) as a colourless glassy solid.

Workup

  1. customThe ethanol was evaporated
  2. extractionThe mixture was extracted with ethyl acetate (2×2 ml)
  3. customThe combined extracts were dried
  4. customevaporated
  5. customThe residue was triturated with iso-hexane

Sources & evidence

ORD record
ord-d85890291d8345cb8ded06d17cd5bb61
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

Loading…