Trifluoroacetic acid → HCID 58674959, compound

HRID 1809481Notes

Reaction equation

HRID 1809481 reaction equation
C([O:5][C:6](=[O:31])[C@@H:7]([N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]1=[O:30])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:22]([NH:21][C:17]1[C:16](=[O:30])[N:15]([C@@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([OH:31])=[O:5])[CH:20]=[CH:19][CH:18]=1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58674951HCID 58674951, compound

Product 1

HCID 58674959HCID 58674959, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-(3-benzoylamino-2-oxo-2H-pyridin-1-yl)-3-phenyl-propionic acid tert-butyl ester (2.07 g, 4.95 mmol) in dichloromethane (25 mL) was cooled to 0° C. Trifluoroacetic acid (25 ml) was added and the resulting mixture allowed to warm to room temperature and stir for 5 hours. The mixture was then concentrated under reduced pressure and the residue re-dissolved in dichloromethane. This process was repeated several times in order to remove excess trifluoroacetic acid. The resulting solid was slurried in diethyl ether, filtered and washed with more diethyl ether. The solid was then dried to constant weight under vacuum. This gave the title product as a white solid (1.61 g, 90%); 1H NMR (400 MHz, CDCl3) δ 3.48 (1H, dd), 3.65 (1H, dd), 5.32 (1H, m), 6.35 (1H, t), 6.80 (1H, m), 7.08 (2H, d), 7.27-7.35 (3H, m), 7.56-7.65 (3H, m), 7.92 (2H, d), 8.65 (1H, d), 9.18 (1H, br s).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. dissolutionthe residue re-dissolved in dichloromethane
  3. customto remove excess trifluoroacetic acid
  4. filtrationfiltered
  5. washwashed with more diethyl ether
  6. customThe solid was then dried to constant weight under vacuum

Sources & evidence

ORD record
ord-44343addb8fc490080ea5006c60a8e00
Source dataset
uspto-grants-2013_01
Patent number
US08362043B2

Reaction notes

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