Sodium Hydroxide → HCID 178515088, compound

HRID 81401Notes

Reaction equation

HRID 81401 reaction equation
[NH:1]1[CH:5]=[C:4](/[CH:6]=[C:7]2\[C:8](=[O:33])[C:9]3[C:14]([CH2:15][CH2:16]\2)=[C:13]([O:17][CH2:18][C@H:19]2[CH2:23][CH2:22][CH2:21][N:20]2[C:24]2[N:32]=[CH:31][N:30]=[C:29]4[C:25]=2[N:26]=[CH:27][NH:28]4)[CH:12]=[CH:11][CH:10]=3)[N:3]=[CH:2]1.[OH-].[Na+]>C(O)(=O)C.O.[Zn]>[NH:1]1[CH:5]=[C:4]([CH2:6][CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[O:17][CH2:18][C@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24]3[N:32]=[CH:31][N:30]=[C:29]4[C:25]=3[N:26]=[CH:27][NH:28]4)[C:8]2=[O:33])[N:3]=[CH:2]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 178515728HCID 178515728, compound

Product 1

HCID 178515088HCID 178515088, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

13.5 100 mg of 2-[1-(1H-imidazol-4-yl)meth-(Z)-ylidene]-5-[(R)-1-(9H-purin-6-yl)pyrrolidin-2-ylmethoxy]-3,4-dihydro-2H-naphthalen-1-one are heated at 80° C. for 30 min. together with 50 mg of zinc powder in 10 ml of conc. acetic acid and 5 ml of water. During this, the colour changes from greenish to yellowish. The batch is adjusted to pH 7 using conc. NaOH solution and extracted to exhaustion with ethyl acetate. The organic phase is dried over magnesium sulfate and freed from solvent in vacuo, giving 50 mg of 2-(1H-imidazol-4-yl-methyl)-5-[(R)-1-(9H-purin-6-yl)pyrrolidin-2-ylmethoxy]-3,4-dihydro-2H-naphthalen-1-one (“A15.1”) as colourless oil. Rt.: 1.405 min; [M+H]+444.2.

Workup

  1. extractionextracted
  2. dry with materialThe organic phase is dried over magnesium sulfate

Sources & evidence

ORD record
ord-91fb0ede20dd4a4fa035cb29d5777cae
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

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