Acetic Acid → HCID 178433372, compound

HRID 445046Notes

Reaction equation

HRID 445046 reaction equation
[C:1]([CH2:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8][CH:9]([C:14](=O)[CH3:15])[C:10](OC)=[O:11])=[CH:6][CH:5]=1)#[N:2].C(=O)(O)O.[NH2:23][C:24]([NH2:26])=[NH:25].C(O)(=O)C>CO.O>[NH2:26][C:24]1[N:25]=[C:10]([OH:11])[C:9]([CH2:8][C:7]2[CH:17]=[CH:18][C:4]([CH2:3][C:1]#[N:2])=[CH:5][CH:6]=2)=[C:14]([CH3:15])[N:23]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 286947Carbonic acid-guanidine (1:1)HCID 59590640Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

Product 1

HCID 178433372HCID 178433372, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred mixture of the crude product from step (i) and guanidine carbonate (128.1 g) in methanol (915 mL) was heated under reflux for 5 hours. The mixture was cooled to room temperature, diluted with water (923 mL) and nuetralised with acetic acid. The mixture was then cooled to 10° C. and the resulting precipitate collected by filtration, washed with methanol (501 mL) and dried under reduced pressure to give the subtitle compound as a solid, 82.4 g; 1H NMR DMSO-d6: δ 10.91 (brs, 1H), 7.20-7.17 (m, 4H), 6.38 (s, 2H), 3.95 (s, 2H), 3.63 (s, 2H), 2.00 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe mixture was then cooled to 10° C.
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed with methanol (501 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4f38c4a77d644a94bd290e0589827f9b
Source dataset
uspto-grants-2013_07
Patent number
US08476288B2

Reaction notes

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