Sodium Bicarbonate → HCID 86607891, compound

HRID 736791Notes

Reaction equation

HRID 736791 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@:3]1([OH:19])[C:15]([O:17][CH3:18])=[O:16].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>[OH:19][C@@:3]1([C:15]([O:17][CH3:18])=[O:16])[C@H:2]([NH:1][S:40]([C:37]2[CH:38]=[CH:39][C:34]([O:33][CH2:32][C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[C:22]([CH3:21])[CH:31]=3)=[CH:35][CH:36]=2)(=[O:41])=[O:42])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochlorideHCID 86607892HCID 86607892, compound

Product 1

HCID 86607891HCID 86607891, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1-tert-butyl 3-methyl (3R,4R)-4-amino-3-hydroxypiperidine-1,3-dicarboxylate (1.63 g, 5.96 mmol), 4-((2-methylquinolin-4-yl)methoxy)benzene-1-sulfonyl chloride hydrochloride (4.6 g, 11.92 mmol, 2.0 eq), CH2Cl2 (100 mL) and saturated NaHCO3 (50 mL) was stirred at room temperature overnight, and then diluted with CH2Cl2. The organic phase was washed with water, then brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel eluting with 50-70% ethyl acetate/hexane to yield 1.65 g (47%) of 1-tert-butyl 3-methyl (3R,4R)-3-hydroxy-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-1,3-dicarboxylate as white solid. MS: (M+H)+=586.1.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialbrine, dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel eluting with 50-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4b32d03f90e5439e80a12bfd72e6c2b6
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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