Acetic Acid → Acetate

HRID 917578Notes

Reaction equation

HRID 917578 reaction equation
O.[C:2]([OH:5])(=[O:4])[CH3:3].CC1O[N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:39]=[CH:40][CH:41]=2)[O:15][CH:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]3=[O:32])=[CH:22][CH:21]=2)=[O:18])[N:8]=1>CO>[C:9]([C:12]1[CH:13]=[C:14]([CH:39]=[CH:40][CH:41]=1)[O:15][CH:16]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]2=[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 962WaterHCID 120425312-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(2-oxopiperidin-1-yl)phenyl]-2-phenylacetamide

Product 2

HCID 175AcetateHCID 98895622-(3-amidinophenoxy)-N-[4-(2-oxopiperidin-1-yl)phenyl]-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg of water-moist Raney nickel and 0.2 ml of acetic acid are added to a solution of 122 mg (0.253 mmol) of 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(2-oxopiperidin-1-yl)phenyl]-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-amidinophenoxy)-N-[4-(2-oxopiperidin-1-yl)phenyl]-2-phenylacetamide, acetate (EMD 388547), ESI 443; IC50(Xa)=3.2×10−8 M; IC50(VIIa)=1.4×10−8 M.

Workup

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

Sources & evidence

ORD record
ord-a0ca3d70de4f41f48cdfa466f1ec4446
Source dataset
uspto-grants-2007_09
Patent number
US07273867B2

Reaction notes

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