Benzeneethanimidamide → HCID 135741926, compound

HRID 2077042Notes

Reaction equation

HRID 2077042 reaction equation
O=[C:2]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4][CH:3]1[C:16]([O:18]CC)=O.[C:21]1([CH2:27][C:28]([NH2:30])=[NH:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C[O-].[Na+]>CO>[CH2:27]([C:28]1[NH:30][C:16](=[O:18])[C:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:7][CH2:8][C:2]=2[N:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 27787BenzeneethanimidamideHCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 135741926HCID 135741926, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Tert-butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate (See WO2006029154, example 1a, p 34) (1.32 g, 4.6 mmol) and 2-phenyl-acetamidine (750 mg, 4.4 mmol) were added to a solution of NaOMe (3.8M, 3.5 mL, 13.2 mmol) in MeOH (15.0 mL) at 0° C. and stirred at 0° C. to room temperature overnight. The reaction was quenched with water, partitioned with ethyl acetate and the phases separated. The combined organics layer were dried over magnesium sulfate, filtered and concentrated in vacuo to provide the crude product as an orange gum. The residue was purified by flash column chromatography eluting with CH2Cl2:ethyl acetate (90:10 to 70:30) to afford the title compound as a white solid (1.30 g, 83% yield).

Workup

  1. customThe reaction was quenched with water
  2. custompartitioned with ethyl acetate
  3. customthe phases separated
  4. dry with materialThe combined organics layer were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide the crude product as an orange gum
  8. customThe residue was purified by flash column chromatography
  9. washeluting with CH2Cl2:ethyl acetate (90:10 to 70:30)

Sources & evidence

ORD record
ord-3b7a3fde9be64598a6d6a53ceaec4ac7
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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