Cyclohexanol → Methyl 4-(3-chloro-4,5-bis(cyclohexyloxy)benzamido)benzoate

HRID 62735Notes

Reaction equation

HRID 62735 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[CH:17]=[C:18]([CH:32]=[C:33]([O:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[C:34]=1[OH:35])[C:19]([NH:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=[O:20].[CH:43]1(O)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:15][C:16]1[CH:17]=[C:18]([CH:32]=[C:33]([O:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[C:34]=1[O:35][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)[C:19]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1)=[O:20]

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67041568HCID 67041568, compound

Product 1

HCID 67041755Methyl 4-(3-chloro-4,5-bis(cyclohexyloxy)benzamido)benzoateYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazo dicarboxylate (63 μL, 0.32 mmol) was added dropwise to a stirring mixture of methyl 4-(3-chloro-5-(cyclohexyloxy)-4-hydroxybenzamido)benzoate (7) (65 mg, 161 μmol), cyclohexanol (34 μL, 0.32 mmol) and triphenylphosphine (84 mg, 0.32 mmol) in THF (2 mL) and the resulting yellow mixture was stirred at RT for 20 h. The reaction was quenched with MeOH (5 mL) and the solvent was removed in vacuo. The residue was purified by silica gel chromatography (40 g, 0-15% EtOAc in iso-hexane) to give the desired methyl 4-(3-chloro-4,5-bis(cyclohexyloxy)benzamido)benzoate (8) (80 mg, 100%): m/z 486 [M+H]+ (ES+); 1H NMR (400-MHz, DMSO-d6) δ: 10.48 (1H, s), 7.97 (2H, d), 7.91 (2H, d), 7.67 (1H, d), 7.53 (1H, d), 4.53 (1H, m), 4.36 (1H, m), 3.84 (3H, m), 1.92 (4H, m), 1.80-1.70 (4H, m), 1.60-1.40 (6H, m), 1.30-1.05 (6H, m).

Workup

  1. customThe reaction was quenched with MeOH (5 mL)
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by silica gel chromatography (40 g, 0-15% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-68fb2cccb0c74de197d0bc93b378206c
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

Loading…