Methanol → HCID 68696541, compound

HRID 1991478Notes

Reaction equation

HRID 1991478 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11][CH:12]([CH3:16])[CH2:13][CH:14]=O.[CH:17]1([N+:23]#[C-:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH2:39])=[O:31])([CH3:28])([CH3:27])[CH3:26].C[OH:41]>>[C:25]([O:29][C:30](=[O:31])[NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N:39]([C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=1)[CH:14]([C:24](=[O:41])[NH:23][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:13][CH:12]([CH3:16])[CH3:11])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 5

HCID 887MethanolHCID 63184-Chlorobenzoic AcidHCID 115523-MethylbutanalHCID 79129Cyclohexyl isocyanideHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 68696541HCID 68696541, compound

Conditions

Temperature
100 °C

Procedure

4-chlorobenzoic acid (43.8 mg, 0.28 mmol, 1.1 equiv.) was added to a solution of 3-methylbutyraldehyde (21.5 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). The reaction mixture was heated in a focussed microwave (CEM Discovery) at 100° C., for 10 minutes with stirring. The solvent was removed in-vacuo and the residue re-dissolved in dichloromethane (2 mL), washed with 1 M aqueous HCl (2 mL), saturated aqueous solution of NaHCO3 (2 mL), dried over Na2SO4 and evaporated under vacuum to afford crude {2-[(4-chloro-benzoyl)-(1-cyclohexylcarbamoyl-3-methyl-butyl)-amino]-phenyl}-carbamic acid tert-butyl ester, 83 mg (61%) as an oil. MS (ES+): 564 (M+H).

Workup

  1. customThe solvent was removed in-vacuo
  2. dissolutionthe residue re-dissolved in dichloromethane (2 mL)
  3. washwashed with 1 M aqueous HCl (2 mL), saturated aqueous solution of NaHCO3 (2 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-51e8d0d178e6480886b81688d6fa3af7
Source dataset
uspto-grants-2010_01
Patent number
US07645785B2

Reaction notes

Loading…