4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride → methyl (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate

HRID 736809Notes

Reaction equation

HRID 736809 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@:3]1([OH:11])[C:7]([O:9][CH3:10])=[O:8].Cl.[CH3:13][C:14]1[CH:23]=[C:22]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1>C(Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[OH:11][C@:3]1([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:5][CH2:6][C@H:2]1[NH:1][S:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([CH3:13])[CH:23]=2)=[CH:27][CH:28]=1)(=[O:33])=[O:34]

Participants

6

Reactant 2

HCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochlorideHCID 86607905rac-methyl (1R,2R)-2-amino-1-hydroxycyclopentane-1-carboxylate

Product 1

HCID 86607906methyl (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylateYield 20.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of methyl (1R,2R)-2-amino-1-hydroxycyclopentanecarboxylate (2.1 mmol) in CH2Cl2 (8 mL) and saturated sodium bicarbonate (8 mL) was added 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (0.88 g, 1.1 eq). The reaction was allowed to stir for 18 h at room temperature, and then taken up in ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified using ilica chromatography eluting with a gradient of 50% -70% ethyl acetate/hexanes afforded methyl (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (0.2 g, 20%). MS: 470.1 (M+H)+

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. washeluting with a gradient of 50% -70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6391f802ec264b89a05d15681f68305a
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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