Sodium Bicarbonate → 4-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

HRID 736751Notes

Reaction equation

HRID 736751 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH2:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4].Cl.[CH3:20][C:21]1[CH:30]=[C:29]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH:11][S:39]([C:36]2[CH:37]=[CH:38][C:33]([O:32][CH2:31][C:29]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:20])[CH:30]=3)=[CH:34][CH:35]=2)(=[O:40])=[O:41])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 592166281-O-tert-butyl 3-O-methyl 4-aminopiperidine-1,3-dicarboxylateHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 688173164-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl esterYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a mixture of 4-amino-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (1.3 g, 5 mmol] and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (1.9 g, 5.50 mmol) in CH2Cl2 (20 mL) was added saturated aqueous NaHCO3 (20 mL) at 0° C. The solution was allowed to warm to 25° C. over 19 h. The reaction was then further diluted in CH2Cl2 (100 mL) and water (30 mL). The organic layer was washed with water (2×50 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide a crude oil (2.6 g). The crude product was purified by Biotage Flash 40M chromatography, eluting with 1:1 ethyl acetate-hexanes, to afford 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as a white solid (1.6 g, 55%). MS: 570 (M+H)+

Workup

  1. washThe organic layer was washed with water (2×50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a crude oil (2.6 g)
  6. customThe crude product was purified by Biotage Flash 40M chromatography
  7. washeluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-e0eb709dbbe84518b6d19cf94ca5ae2f
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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