Triethylamine → HCID 86664942, compound

HRID 1620393Notes

Reaction equation

HRID 1620393 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][C:10]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.Cl.Cl.[NH2:34][CH2:35][C@@H:36]([N:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:37]([O:39][CH3:40])=[O:38]>ClCCl.CN(C)C=O>[CH3:9][C:10]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([NH:34][CH2:35][C@@H:36]([N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:37]([O:39][CH3:40])=[O:38])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochlorideHCID 86664943HCID 86664943, compound

Product 1

HCID 86664942HCID 86664942, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

7.2 ml (51.5 mmol) of triethylamine and then 5.9 g (15.5 mmol) of 4-(2-methylquinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride are added to a solution of 3.34 g (12.9 mmol) of methyl (R)-3-amino-2-piperidin-1-ylpropanoate dihydrochloride in 30 ml of dichloromethane and 30 ml of dimethylformamide cooled beforehand using an ice bath. The reaction medium is stirred at ambient temperature for 3 h 30, hydrolyzed, and then diluted with dichloromethane. The product is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 50/50 heptane/ethyl acetate mixture. 4 g (62%) of methyl (R)-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-ylpropanoate are obtained in the form of a white solid.

Workup

  1. temperaturecooled beforehand
  2. extractionThe product is extracted with dichloromethane
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-3fa98b3146964a4abb55329623af935a
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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