Acetic Acid → HCID 178451657, compound

HRID 1713111Notes

Reaction equation

HRID 1713111 reaction equation
C[O-].[Na+].[CH:4]([NH2:6])=[NH:5].O=[C:8]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10][CH:9]1[C:22](OC)=[O:23].C(O)(=O)C>CO>[OH:23][C:22]1[C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[N:6]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 68047FormamidineHCID 10942334Sodium MethoxideHCID 57479414HCID 57479414, compound

Product 1

HCID 178451657HCID 178451657, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of NaOMe in MeOH (13.6 mL, 25% in MeOH, 59.5 mmol) is added to a stirred solution of formamidine (2.2 g, 21 mmol) in MeOH (50 ml) at rt. The mixture is stirred for 15 min. 1-tert-Butyl 4-methyl 5-oxoazepane-1,4-dicarboxylate (5 g, 7.5 mmol) is added and the mixture is stirred at rt overnight. Acetic acid (2.33 g, 38.5 mmol) is added and the solvent is removed in vacuo. Water (30 ml) is added to the residue and the solution is extracted with DCM (3×30 ml). The combined extracts are washed with brine (40 ml), dried (Na2SO4) and evaporated, to provide a yellow solid that is used in the next step without further purification.

Workup

  1. stirringthe mixture is stirred at rt overnight
  2. customthe solvent is removed in vacuo
  3. additionWater (30 ml) is added to the residue
  4. extractionthe solution is extracted with DCM (3×30 ml)
  5. washThe combined extracts are washed with brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto provide a yellow solid that
  9. customis used in the next step without further purification

Sources & evidence

ORD record
ord-bbf2991210f548aa9c16d95d154514df
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

Loading…