Dichloromethane → HCID 58508921, compound

HRID 454630Notes

Reaction equation

HRID 454630 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(Cl)Cl.Cl.[OH:12][C:13]1[CH:37]=[C:36]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:35]=[CH:34][C:14]=1[C:15]([NH:17][C:18]1[CH:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])=[O:16]>N1C=CC=CC=1>[C:1]([N:42]1[CH2:41][CH2:40][CH:39]([O:38][C:36]2[CH:35]=[CH:34][C:14]([C:15]([NH:17][C:18]3[CH:27]=[C:26]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])=[O:16])=[C:13]([OH:12])[CH:37]=2)[CH2:44][CH2:43]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 66990896HCID 66990896, compound

Product 1

HCID 58508921HCID 58508921, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Under ice-cooling, pyridine (0.010 mL) and acetic anhydride (4.0 μL) were sequentially added to a methylene chloride (1 mL) suspension of the obtained methyl 2-(2-hydroxy-4-(piperidin-4-yloxy)benzamido)-4-phenylbenzoate hydrochloride (0.017 g), followed by stirring at room temperature for 1 hour. Pyridine (0.49 mL) and acetic anhydride (4.0 μL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and a 10% aqueous solution of citric acid and ethyl acetate were added to the residue. The organic layer was separated, washed with a 10% aqueous solution of citric acid, and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.016 g of methyl 2-(4-((1-acetylpiperidin-4-yl)oxy)-2-hydroxybenzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. stirringby stirring at room temperature for 1 hour
  3. customThe solvent was evaporated under reduced pressure
  4. additiona 10% aqueous solution of citric acid and ethyl acetate were added to the residue
  5. customThe organic layer was separated
  6. washwashed with a 10% aqueous solution of citric acid
  7. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9551506ac18f434cacedd8f7eba6ce75
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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