Trifluoroacetic acid → HCID 16036642, compound

HRID 2234167Notes

Reaction equation

HRID 2234167 reaction equation
[OH:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[C:5]([CH2:12][CH2:13][NH:14][CH2:15][CH2:16][N:17]([CH2:31][CH:32]2[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]2)[C:18](=[O:30])[CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[OH:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[C:5]([CH2:12][CH2:13][NH:14][CH2:15][CH2:16][N:17]([CH2:31][CH:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]2)[C:18](=[O:30])[CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16036641HCID 16036641, compound

Product 1

HCID 16036642HCID 16036642, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[{2-[2-(4-hydroxy-2-oxo-2,3-dihydro-benzothiazol-7-yl)-ethylamino]-ethyl}-(3-phenethyloxy-propionyl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (Example 1, 0.2 g) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL) and the reaction mixture was stirred for 30 minutes and then concentrated. The residue was dissolved in methanol (5 mL) and purified by reverse phase HPLC eluting with 5% to 95% acetonitrile in 0.2% trifluoroacetic acid. The fractions containing the product were concentrated and dissolved in methanol where 4N hydrogen chloride in 1,4-dioxane was added. The mixture was concentrated and the residue was triturated with ether, the ether was decanted and further concentration afforded the titled compound (0.13 g) as a hygroscopic solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol (5 mL)
  3. custompurified by reverse phase HPLC
  4. washeluting with 5% to 95% acetonitrile in 0.2% trifluoroacetic acid
  5. additionThe fractions containing the product
  6. concentrationwere concentrated
  7. dissolutiondissolved in methanol where 4N hydrogen chloride in 1,4-dioxane
  8. additionwas added
  9. concentrationThe mixture was concentrated
  10. customthe residue was triturated with ether
  11. customthe ether was decanted
  12. concentrationfurther concentration

Sources & evidence

ORD record
ord-17f74580caf0473e962111b2548d54d1
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

Loading…