Acetic Acid → Acetate

HRID 1268821Notes

Reaction equation

HRID 1268821 reaction equation
O.[C:2]([OH:5])(=[O:4])[CH3:3].CC1O[N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:36]=[CH:37][CH:38]=2)[O:15][CH:16]([CH2:33][CH2:34][CH3:35])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:30][CH2:29][CH2:28][S:27]3(=[O:32])=[O:31])=[CH:22][CH:21]=2)=[O:18])[N:8]=1>CO>[C:9]([C:12]1[CH:13]=[C:14]([CH:36]=[CH:37][CH:38]=1)[O:15][CH:16]([CH2:33][CH2:34][CH3:35])[C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:30][CH2:29][CH2:28][S:27]2(=[O:31])=[O:32])=[CH:24][CH:25]=1)=[O:18])(=[NH:8])[NH2:10].[C:2]([O-:5])(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962Water2×HCID 114088012-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide

Product 2

HCID 175AcetateHCID 102029832-(3-amidinophenoxy)-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g of water-moist Raney nickel, 0.5 ml of glacial acetic acid and 0.5 ml of water are added to a solution of 200 mg (0.425 mmol) of 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]-valeramide in 10 ml of methanol, and the mixture is hydrogenated. The reaction mixture is filtered, and the filtrate is evaporated, giving 2-(3-amidinophenoxy)-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide, acetate (“AA”) as a colourless solid; ESI 431.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-619b99d23f764e4893328366fac9ad95
Source dataset
uspto-grants-2007_04
Patent number
US07199133B2

Reaction notes

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