Trifluoroacetic anhydride → HCID 58109500, compound

HRID 2037519Notes

Reaction equation

HRID 2037519 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][C:31]([NH2:33])=O)([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:34])[CH3:16])=[CH:11][CH:10]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl.CCN(C(C)C)C(C)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][C:31]#[N:33])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:34])[CH3:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 53473234HCID 53473234, compound

Product 1

HCID 58109500HCID 58109500, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)acetamide (60 mg, 0.128 mmol) in anhydrous CH2Cl2 (4 mL) and DIEA (0.3 mL) was added TFAA (55 mg, 0.256 mmol) at 0□. The mixture was stirred for 2 h. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC to afford 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)acetonitrile (40 mg, 82%). LC-MS Method 3 tR=1.52, min, m/z=451, 473; 1H NMR (CDCl3): 1.56 (m, 3H), 2.40 (m, 2H), 2.54 (m, 1H), 2.82-2.98 (m, 2H), 3.04 (m, 1H), 5.64 (m, 1H), 6.83-6.94 (m, 5H), 7.09 (m, 2H), 7.21 (m, 1H), 7.28 (m, 1H), 7.37 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-acb57bc1d55e4d3daa551561ae0b465b
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…