Formamidine acetate → HCID 58653691, compound

HRID 1676078Notes

Reaction equation

HRID 1676078 reaction equation
[NH2:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[NH:4][C@@H:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].[C:24](O)(=O)C.C(N)=N>C(OCCO)C>[N+:21]([C:19]1[CH:18]=[CH:17][C:3]2[N:4]([C@@H:5]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH:24]=[N:1][C:2]=2[CH:20]=1)([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 58653652HCID 58653652, compound

Product 1

HCID 58653691HCID 58653691, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl (3R)-3-(2-amino-4-nitroanilino)-3-phenylpropanoate (2.10 g, 6.7 mmol) in 2-ethoxyethanol (65 mL) was added formamidine acetate (2.8 g, 26.6 mmol), and the mixture heated to 85° C. for 5 hours. The mixture was then cooled to room temperature, evaporated in vacuo, and the residue purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (95:5) to afford a mixture of the title compound and the corresponding 2-ethoxyethanol ester, which was used directly without any additional purification. [LCMS (Method C, Mobile Phase I) RT=2.86 mins (broad), MH+ 326 (Me-ester) and 384 (EtOCH2CH2-ester)].

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customevaporated in vacuo
  3. customthe residue purified by flash column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and methanol (95:5)
  5. customto afford

Sources & evidence

ORD record
ord-711cfb2da18e472fac95ce21dda2fd4b
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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