Fumaric Acid → HCID 86586960, compound

HRID 2297727Notes

Reaction equation

HRID 2297727 reaction equation
[C:1]([S:4][CH2:5][CH2:6][N:7]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:8](=[O:27])[NH:9][C@@H:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])(=[O:3])[CH3:2].[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40]>CCOCC.CO>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40].[C:1]([S:4][CH2:5][CH2:6][N:7]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:8](=[O:27])[NH:9][C@@H:10]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:11]([N:13]1[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 59923444HCID 59923444, compound

Product 1

HCID 86586960HCID 86586960, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-[(2S)-2-[3-[2-(Acetylthio)ethyl]-3-phenethylureido]-3-phenylpropionyl]-4-methylpiperazine (Compound No. 27-2, 16.39 g) is dissolved in ether (150 ml), and a solution of fumaric acid (3.83 g) in methanol (100 ml) is added thereto under ice cooling. The reaction mixture is concentrated under reduced pressure, the resulting oily matter is dissolved in diethyl ketone (40 ml), and the solution is allowed to stand in a refrigerator overnight to give 9.04 g (45%) of the titled compound (Compound No. 35-1) as crystals.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe resulting oily matter is dissolved in diethyl ketone (40 ml)
  3. customto stand in a refrigerator overnight

Sources & evidence

ORD record
ord-3284911b85aa4bbdbff67aaab52dd234
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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