Formamidine acetate → HCID 67354345, compound

HRID 1676033Notes

Reaction equation

HRID 1676033 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[NH:4][C@@H:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:24](O)(=O)C.C(N)=N>C(OCCO)C>[N:4]1([C@@H:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]=2[N:1]=[CH:24]1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 67352508HCID 67352508, compound

Product 1

HCID 67354345HCID 67354345, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (3R)-3-(2-aminoanilino)-3-phenylpropanoate (78 mg, 250 μmol) in 2-ethoxyethanol (2 mL), was added formamidine acetate (41 mg, 394 μmol). The solution was heated at 80° C. for 1.75 hours, and was then evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (98:2) to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=6.30 min, MH+ 323].

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane and methanol (98:2)

Sources & evidence

ORD record
ord-53c04b5000d642dda4b358dbdc8abd50
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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