Triethylamine → HCID 59376160, compound

HRID 2093736Notes

Reaction equation

HRID 2093736 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][NH:8][C@H:7]1[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=1)=[O:5])[CH3:2].CCN(CC)CC.[CH3:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:36](=[O:37])[C:35]2[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=2[CH3:33])[C@H:7]1[C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])=[CH:16][CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 59376099ethyl (2R,3S)-2-(4-((tert-butoxycarbonyl)amino)phenyl)piperidine-3-carboxylate

Product 1

HCID 59376160HCID 59376160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of the (2R,3S)-2-(4-tert-Butoxycarbonylaminophenyl)-piperidine-3-carboxylic acid ethyl ester prepared above (600 mg, 1.72 mmol) in dry CH2Cl2 (5 mL) containing Et3N (480 μL, 3.44 mmol) was added 2-methylbenzoyl chloride (266 mg, 1.72 mmol) and the mixture was stirred at room temperature for over night. The reaction mixture was then diluted with CH2Cl2 (20 mL), washed with 1 N aqueous HCl, water, and brine. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure to give (2R,3S)-2-(4-tert-Butoxycarbonylaminophenyl)-1-(2-methylbenzoyl)piperidine-3-carboxylic acid ethyl ester in quantitative yield and the crude product was used as such in the next step.

Workup

  1. washwashed with 1 N aqueous HCl, water, and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f229afda849a408e8514c34462db59f7
Source dataset
uspto-grants-2013_05
Patent number
US08445515B2

Reaction notes

Loading…