Trifluoroacetic acid → HCID 86759196, compound

HRID 987216Notes

Reaction equation

HRID 987216 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[N:15]([C:16](=[O:26])[CH:17]=[C:18]([C:23]([OH:25])=[O:24])[CH:19]=2)[CH:14]=1)=O)(C)(C)C.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>ClCCl>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[N:15]([C:16](=[O:26])[CH:17]=[C:18]([C:23]([OH:25])=[O:24])[CH:19]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22988031HCID 22988031, compound

Product 1

HCID 86759196HCID 86759196, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7-(3-tert-butoxycarbonylamino-propoxy)-4-oxo-4H-quinolizine-2-carboxylic acid (18 mg, 0.050 mmol) in anhydrous dichloromethane (1 ml) under nitrogen atmosphere was added trifluoroacetic acid (1 ml). The mixture was stirred for 2 hours at room temperature, concentrated and triturated with ether to give 17.3 mg (92% yield) of desired compound as a yellow solid which was characterized by 1HNMR (300 MHz, CD3OD) δ: 2.22-2.29 (m, 2H), 3.20-3.23 (m, 2H), 4.28-4.31 (m, 2H) 7.09 (d, J=1.5 Hz, 1H), 7.46-7.49 (dd, J=9.5 and 2.5 Hz, 1H) 7.52 (s, 1H), 7.90 (d, J=9.5 Hz, 1H), 8.71 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customtriturated with ether

Sources & evidence

ORD record
ord-5c1128388444452495ddf789be363940
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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