Acetic Acid → 3,5-Dioxohexanoic acid

HRID 917574Notes

Reaction equation

HRID 917574 reaction equation
[OH2:1].[C:2]([OH:5])(=[O:4])[CH3:3].O[NH:7][C:8]([C:10]1[CH:11]=[C:12]([NH:16][CH:17]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=2)=[O:19])[CH:13]=[CH:14][CH:15]=1)=[NH:9]>CO>[C:8]([C:10]1[CH:11]=[C:12]([NH:16][CH:17]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[CH:23][CH:22]=2)=[O:19])[CH:13]=[CH:14][CH:15]=1)(=[NH:7])[NH2:9].[CH3:38][C:33]([CH2:17][C:18]([CH2:3][C:2]([OH:5])=[O:4])=[O:19])=[O:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178513312HCID 178513312, compound

Product 2

HCID 54598443,5-Dioxohexanoic acidHCID 12042523HCID 12042523, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

500 mg of water-moist Raney nickel and 0.1 ml of acetic acid are added to a solution of 150 mg (0.337 mmol) of 2-[3-(N-hydroxyamidino)phenylamino]-N-(4-morpholin-4-ylphenyl)-2-phenylacetamide in 5 ml of methanol, and the mixture is hydrogenated at room temperature and atmospheric pressure for 18 hours. The reaction mixture is filtered, and the residue is evaporated, giving 2-(3-amidinophenylamino)-N-(4-morpholin-4-ylphenyl)-2-phenylacetamide, triacetate, ESI 430; IC50 (Xa)=3.4×10−8 M; IC50 (VIIa)=2.2×10−8 M;

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe reaction mixture is filtered
  3. customthe residue is evaporated

Sources & evidence

ORD record
ord-b8affb5a4cdc47ec909f1398f03ab40d
Source dataset
uspto-grants-2007_09
Patent number
US07273867B2

Reaction notes

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