Trifluoroacetic acid → HCID 68900430, compound

HRID 897348Notes

Reaction equation

HRID 897348 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([N:21]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23][S:22]3(=[O:36])=[O:35])[N:11]=2)=[O:9])=[CH:4][CH:3]=1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>C(Cl)Cl>[F:39][C:40]([F:45])([F:44])[C:41]([O-:43])=[O:42].[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([N:21]3[CH2:27][CH2:26][NH2+:25][CH2:24][CH2:23][S:22]3(=[O:35])=[O:36])[N:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22346428HCID 22346428, compound

Product 1

HCID 68900430HCID 68900430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-1,2,5-thiadiazepane-5-carboxylate 1,1-dioxide (0.088 g, 0.185 mmol) in methylene chloride (5 mL) was treated with trifluoroacetic acid (2 mL) at room temperature. After 6 hr the solvent was evaporated in vacuo and the residue purified by preparative HPLC (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.

Workup

  1. customAfter 6 hr the solvent was evaporated in vacuo
  2. customthe residue purified by preparative HPLC (Gilson semi preparative HPLC system
  3. washa YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

Sources & evidence

ORD record
ord-14661d6bec2a455385745d821b6e11b3
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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