Acetic Acid → HCID 67041568, compound

HRID 62734Notes

Reaction equation

HRID 62734 reaction equation
Br.C(O)(=O)C.C([O:13][C:14]1[C:32]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:31][C:17]([C:18]([NH:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)=[O:19])=[CH:16][C:15]=1[Cl:40])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:40][C:15]1[CH:16]=[C:17]([CH:31]=[C:32]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:14]=1[OH:13])[C:18]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=1)=[O:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 67041734HCID 67041734, compound

Product 1

HCID 67041568HCID 67041568, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

45% hydrogen bromide in acetic acid (26 μL, 0.20 mmol) was added to a stirring mixture of methyl 4-(4-(benzyloxy)-3-chloro-5-(cyclohexyloxy)benzamido)benzoate (6) (20 mg, 40 μmol) in TFA (3 mL) and the mixture was stirred at RT for 1 h. The mixture was partitioned between water (15 mL) and EtOAc (15 mL) and the phases were separated. The organic solution was washed with water (10 mL), dried over MgSO4 and the solvent was removed in vacuo to give methyl 4-(3-chloro-5-(cyclohexyloxy)-4-hydroxybenzamido)benzoate (7) (16 mg, 92%): m/z 402 [M−H]− (ES−); 1H NMR (400-MHz, DMSO-d6) δ: 10.37 (1H, s), 7.94 (4H, m), 7.68 (1H, d), 7.54 (1H, d), 4.40 (1H, m), 3.84 (3H, s), 1.94 (2H, m), 1.83-1.73 (2H, m), 1.57-1.45 (3H, m), 1.40-1.20 (3H, m).

Workup

  1. customThe mixture was partitioned between water (15 mL) and EtOAc (15 mL)
  2. customthe phases were separated
  3. washThe organic solution was washed with water (10 mL)
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b9cfc429afbb4095a415e04db1a2cdbf
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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