Sodium Bicarbonate → HCID 68821282, compound

HRID 736762Notes

Reaction equation

HRID 736762 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]1[NH2:19])=[O:5])[CH3:2].Cl.[CH3:21][C:22]1[CH:31]=[C:30]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]1[NH:19][S:40]([C:37]1[CH:38]=[CH:39][C:34]([O:33][CH2:32][C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:21])[CH:31]=2)=[CH:35][CH:36]=1)(=[O:41])=[O:42])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23590626HCID 23590626, compoundHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 68821282HCID 68821282, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a mixture of 2.89 g (10.62 mmol) of 3-amino-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester [WO 01/70673, Example 134] and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (4.0 g, 11.8 mmol) in CH2Cl2 (40 mL) at 0° C. was added saturated aqueous NaHCO3 (40 mL). The solution was allowed to warm to 25° C. over 19 h. The reaction was then diluted with CH2Cl2 (100 mL) and water (30 mL), the organic layer was washed with water (2×50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Biotage Flash 40M chromatography, eluting with 1:2 ethyl acetate-hexanes, to afford 3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester as a white solid (1.6 g, 25.8%). MS: 584 (M+H)+.

Workup

  1. washthe organic layer was washed with water (2×50 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by Biotage Flash 40M chromatography
  6. washeluting with 1:2 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-499c9177a7ff4fdb81655efe17f52bf1
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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