Trifluoroacetic acid → HCID 69695297, compound

HRID 1355653Notes

Reaction equation

HRID 1355653 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:12][C:13]([N:15]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=2)[C@H:18]([NH:29]C(OC(C)(C)C)=O)[CH2:17][C@@H:16]1[CH:37]1[CH2:39][CH2:38]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[OH-].[Na+]>ClCCl>[C:8]([O:12][C:13]([N:15]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([F:27])([F:26])[F:28])=[CH:22][CH:23]=2)[C@H:18]([NH2:29])[CH2:17][C@@H:16]1[CH:37]1[CH2:38][CH2:39]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69694295HCID 69694295, compound

Product 1

HCID 69695297HCID 69695297, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.4 g) was added in portions to a solution of cis-4-tert-butoxycarbonylamino-2-cyclopropyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (Example 107B) (3.4 g; 7.4 mmol) in 150 ml dichloromethane, and the reaction was stirred until no starting material was observed by thin-layer chromatography. A small amount of 1N NaOH was added and the reaction mixture was dried (MgSO4), filtered and concentrated. Chromatography on silica gel (50% ethyl acetate:hexane through 5% MeOH:dichloromethane) afforded the title product (1.0 g). 1H NMR (CDCl3) δ 1.5 (s, 9H), 1.7 (m, 1H), 2.5 (m, 1H), 4.1 (q, 1H), 7.6 (m, 3H).

Workup

  1. dry with materialthe reaction mixture was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1f6adcbd2136457c9d64c06ae804b7ef
Source dataset
uspto-grants-2003_07
Patent number
US06586448B1

Reaction notes

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