Trifluoromethanesulfonic acid → 6-Chloro-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 1745858Notes

Reaction equation

HRID 1745858 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]([Cl:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.[F:37][C:38]([S:41](O)(=[O:43])=[O:42])([F:40])[F:39]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[N:8]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[C:9]2[C:14]([C:15]=1[O:16][S:41]([C:38]([F:40])([F:39])[F:37])(=[O:43])=[O:42])=[CH:13][C:12]([Cl:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 81531DiisopropylethylamineHCID 546885376-Chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 210202526-Chloro-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-quinoline-3-carboxylic acid ethyl esterYield 90.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 10 (63.0 mg, 0.16 mmol), DMAP (7.0 mg, 0.054 mmol), and diisopropylethylamine (19.0 mg, 0.15 mmol) in anhydrous CH2Cl2 was treated with trifluoromethylsulfonic acid (78.0 mg, 0.28 mmol). The reaction was stirred at room temperature for 30 min and concentrated. Chromatography (SiO2, 3:1 Hex/EtOAc) gave 11 (75.0 mg, 88%) as a amorphous solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-1d1b24fbbea04195bd65c159a1997ac5
Source dataset
uspto-grants-2006_03
Patent number
US07019141B2

Reaction notes

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