Trifluoroacetic anhydride → HCID 58109635, compound

HRID 2037505Notes

Reaction equation

HRID 2037505 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@:19]([CH2:28][CH2:29][C:30]([NH2:32])=O)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:18][C:17]3=[O:33])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@:19]([CH2:28][CH2:29][C:30]#[N:32])([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[O:18][C:17]3=[O:33])[CH3:15])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 59635802HCID 59635802, compound

Product 1

HCID 58109635HCID 58109635, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((R)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propanamide (110 mg, 0.25 mmol) and DIEA (170 mg, 1.05 mmol) in anhydrous CH2Cl2 (5 mL) was added TFAA (158 mg, 0.75 mmol) at 0° C. The mixture was stirred for 2 h. The solvent was removed under reduced pressure, and the residue was purified by preparative HPLC to afford 3-((R)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propanenitrile (8 mg, yield 10%). LC-MS Method 3 tR=1.458, min, m/z=429.2; 1H NMR (CDCl3): 1.52 (d, 3H), 2.01 (m, 1H), 2.14 (m, 2H), 2.29 (m, 3H), 2.53 (m, 2H), 2.90 (m, 1H), 5.62 (m, 1H), 6.93 (m, 2H), 7.04 (m, 2H), 7.16-7.25 (m, 2H), 7.30-7.47 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-8371848507f34a589c937990144c27cb
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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