Benzoic Acid → HCID 68698724, compound

HRID 1991476Notes

Reaction equation

HRID 1991476 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]1([CH:16]=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH:18]1([N+:24]#[C-:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:26]([O:30][C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[NH2:40])=[O:32])([CH3:29])([CH3:28])[CH3:27].Cl.C[OH:43]>>[C:26]([O:30][C:31](=[O:32])[NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N:40]([C:1](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:16]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[C:25](=[O:43])[NH:24][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 6

HCID 243Benzoic AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 16275CyclohexanecarboxaldehydeHCID 79129Cyclohexyl isocyanideHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 68698724HCID 68698724, compound

Procedure

Benzoic acid (34.2 mg, 0.28 mmol, 1.1 equiv.) was added to a solution of cyclohexanecarbaldehyde (42.6 mg, 0.38 mmol, 1.5 equiv.), cyclohexyl isocyanide (30.6 mg, 0.28 mmol, 1.1 equiv.) and N-tert-butoxycarbonyl phenylene diamine (52.1 mg, 0.25 mmol, 1 equiv.) in methanol (0.5 mL) and the mixture was stirred at room temperature for 16 hours. 1 M aqueous HCl (1 mL) was added and the mixture was extracted with dichloromethane (2×1 mL). Na2SO4 (50 mg), PS-carbonate (4 mmol/g, 50 mg) and PS-TsNHNH2 (4 mmol/g, 50 mg) were added to the organic phase and the mixture was shaken for 60 minutes. The mixture was filtered and the filtrate evaporated in-vacuo. Purification by preparative HPLC (gradient elution: water/acetonitrile with 0.1% trifluoroacetic acid) afforded {2-[benzoyl-(cyclohexyl-cyclohexylcarbamoyl-methyl)-amino]phenyl}-carbamic acid tert-butyl ester, 64 mg (47%) as a yellow oil. MS (ES+): 534 (M+H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×1 mL)
  2. additionNa2SO4 (50 mg), PS-carbonate (4 mmol/g, 50 mg) and PS-TsNHNH2 (4 mmol/g, 50 mg) were added to the organic phase
  3. stirringthe mixture was shaken for 60 minutes
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated in-vacuo
  6. customPurification
  7. washby preparative HPLC (gradient elution: water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-3a4e674e708f41348b1de80330bbcb9d
Source dataset
uspto-grants-2010_01
Patent number
US07645785B2

Reaction notes

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