Cesium carbonate → HCID 86607910, compound

HRID 736814Notes

Reaction equation

HRID 736814 reaction equation
[F:1][C@:2]1([C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=[C:32]([CH3:40])[CH:31]=1>CN(C=O)C.C(OCC)(=O)C>[F:1][C@:2]1([C:18]([O:20][CH3:21])=[O:19])[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][CH2:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]=[C:32]([CH3:40])[CH:31]=2)=[CH:13][CH:12]=1)(=[O:9])=[O:10]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 115357194-(Chloromethyl)-2-methylquinolineHCID 86607909HCID 86607909, compound

Product 1

HCID 86607910HCID 86607910, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (1R,2R)-1-fluoro-2-{[(4-hydroxyphenyl)sulfonyl]amino}cyclopentanecarboxylate (0.42 g, 1.3 mmol, 1 eq) in DMF (4 mL) was added cesium carbonate (0.86 g, 2 eq) followed by 4-chloromethyl-2-methyl-quinoline. The brown reaction mixture was stirred for 3 days, and then taken up in ethyl acetate, washed with brine, dried over Na2SO4, filtered and concentrated. Purification using silica chromatography eluting with 40-70% ethyl acetate/hexanes afforded methyl (1R,2R)-1-fluoro-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate as an off white solid (0.23 g, 41%). MS: 473.1 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification
  6. washeluting with 40-70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-157e08fb08e64eda8f77ab0e506830b8
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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