Hydrochloric Acid → HCID 57879309, compound

HRID 1673404Notes

Reaction equation

HRID 1673404 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]1(C)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:22]([NH:30][C:31]1[CH:40]=[C:39]([OH:41])[CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(O)CCCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(OCC)(=O)C.O1CCCC1>[C:22]([NH:30][C:31]1[CH:40]=[C:39]([O:41][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 57879368Methyl 2-(benzamido)-4-hydroxybenzoateHCID 66880968DIAD toluene

Product 1

HCID 57879309HCID 57879309, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.20 mL of 40% diisopropyl azodicarboxylate /toluene was added dropwise to 1 mL of tetrahydrofuran solution containing 90 mg of methyl 2-(benzamido)-4-hydroxybenzoate, 0.035 mL of cyclohexanol and 0.10 g of triphenylphosphine at room temperature, and stirred at the same temperature for 5 hours. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to obtain 36 mg of methyl 2-(benzamido)-4-(cyclohexyloxy)benzoate as while solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. washafter washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution sequentially
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-bc7bf9808725485b991632955cb14515
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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