Methanol → (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid

HRID 736810Notes

Reaction equation

HRID 736810 reaction equation
[OH:1][C@:2]1([C:30]([O:32]C)=[O:31])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9].[OH-].[Na+].CO>C1COCC1>[OH:1][C@:2]1([C:30]([OH:32])=[O:31])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:15][CH:16]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86607906methyl (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate

Product 1

HCID 68818579(1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acidYield 438.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (0.19 g, 0.4 mmol ) in THF (2 mL) was added sodium hydroxide solution (5 M, 2 mL) and methanol (2 mL) to make the reaction mixture homogenous. The reaction was stirred for 5 h, and then the MeOH/THF was removed in vacuo. The reaction was quenched with a pH 3 sodium phoshphate buffer. Ethyl acetate was added to this mixture, resulting in the formation of a white precipitate which was isolated by filtration to afford (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid (0.8 g, 42%) as a white solid. MS: 457.0 (M+H)+

Workup

  1. customthe MeOH/THF was removed in vacuo
  2. customThe reaction was quenched with a pH 3 sodium
  3. additionEthyl acetate was added to this mixture
  4. customresulting in the formation of a white precipitate which
  5. customwas isolated by filtration

Sources & evidence

ORD record
ord-606168a270cb42d4b550939ff3725d68
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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