Trifluoroacetic acid → HCID 11540489, compound

HRID 1809484Notes

Reaction equation

HRID 1809484 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][CH:8]([NH:13][C:14](=[O:39])[C@@H:15]([N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]1=[O:38])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9](=[O:12])[CH2:10][F:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:30]([NH:29][C:25]1[C:24](=[O:38])[N:23]([C@@H:15]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:14]([NH:13][CH:8]([C:9](=[O:12])[CH2:10][F:11])[CH2:7][C:6]([OH:40])=[O:5])=[O:39])[CH:28]=[CH:27][CH:26]=1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58674963HCID 58674963, compound

Product 1

HCID 11540489HCID 11540489, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3(R,S)-[2(S)-(3-benzoylamino-2-oxo-2H-pyridin-1-yl)-3-phenyl-propionylamino]-5-fluoro-4-oxo-pentanoic acid tert-butyl ester (776 mg, 1.41 mmol) in dichloromethane (6 mL) was cooled to 0° C. Trifluoroacetic acid (2 ml) was added and the resulting mixture allowed to warm to room temperature and stir for 3 hours. The mixture was then concentrated under reduced pressure and the residue redissolved in dichloromethane. This process was repeated several times in order to remove excess trifluoroacetic acid. The solid was then dried to constant weight under vacuum. This gave the title product as a pink solid (627 mg, 90%); 1H NMR (400 MHz, d6-DMSO) δ 2.59-2.95 (2H, m), 3.34-3.47 (2H, m), 4.30-4.81 (2H, m), 5.15-5.33 (2H, m), 5.87-6.09 (1H, m), 6.38 (1H, t), 7.15-7.32 (5H, m), 7.60-7.78 (4H, m), 7.92 (2H, d), 8.17-8.21 (1H, m), 9.01-9.11 (1H, m), 9.28 (1H, m), 12.51 (1H, br s); 19F NMR (376 MHz, d6-DMSO, proton-decoupled) δ−226.8, 232.6; M+H 494.4, M−H 492.4.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. dissolutionthe residue redissolved in dichloromethane
  3. customto remove excess trifluoroacetic acid
  4. customThe solid was then dried to constant weight under vacuum

Sources & evidence

ORD record
ord-69cffaaf7dc046289a42bb11c4dfa8fc
Source dataset
uspto-grants-2013_01
Patent number
US08362043B2

Reaction notes

Loading…