Acetic Acid → HCID 178433211, compound

HRID 916655Notes

Reaction equation

HRID 916655 reaction equation
C[O-].[Na+].C(O)(=O)C.[CH:8]([NH2:10])=[NH:9].C[O:12][C:13](=O)[CH:14]([CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15](=O)[CH3:16].C(O)(=O)C>CO>[CH2:21]([O:20][CH2:19][CH2:18][C:14]1[C:13]([OH:12])=[N:9][CH:8]=[N:10][C:15]=1[CH3:16])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 119536662-(2-Benzyloxy-ethyl)-3-oxo-butyric acid methyl ester

Product 1

HCID 178433211HCID 178433211, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOMe (2.75 g, 50 mmol) is added to a stirred solution of formamidine acetate (25 mmol) in MeOH (75 ml) at room temperature. The mixture is stirred for 15 minutes. 2-(2-Benzyloxy-ethyl)-3-oxo-butyric acid methyl ester (20 mmol) is added and the mixture is stirred at room temperature overnight. Acetic acid (1.5 g, 20 mmol) is added and the solvent is removed in vacuo. Water (30 ml) is added to the residue and the mixture is extracted with 2-butanone (3×30 ml). The combined extracts are washed with brine (40 ml), dried (Na2SO4) and evaporated, to provide a yellow solid (160).

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. customthe solvent is removed in vacuo
  3. additionWater (30 ml) is added to the residue
  4. extractionthe mixture is extracted with 2-butanone (3×30 ml)
  5. washThe combined extracts are washed with brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-252e2ffd0f3a48529d08ae0d8875ca3a
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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