HCID 66857525, compound → HCID 66856519, compound

HRID 2037529Notes

Reaction equation

HRID 2037529 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][CH2:31][N:32](C)[C:33](=O)OC(C)(C)C)([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:41])[CH3:16])=[CH:11][CH:10]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[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]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)([CH2:30][CH2:31][NH:32][CH3:33])[O:19][C:18]2=[O:41])[CH3:16])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 66857525HCID 66857525, compound

Product 1

HCID 66856519HCID 66856519, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl(methyl)carbamate (73 mg, 0.13 mmol) in TFA/CH2Cl2 (20%, 6 mL) was stirred at 0° C. for 1 h. After the material was consumed, the solution was concentrated to give residue, which was purified by preparative TLC followed by preparative HPLC to give (R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-(methylamino)ethyl)-1,3-oxazinan-2-one (13 mg, 21%). LC-MS Method 3 tR=1.10, min, m/z=469; 1H NMR (CDCl3): 1.50 (d, 3H), 2.25 (m, 4H), 2.37 (m, 1H), 2.60 (m, 3H), 2.81 (m, 1H), 2.98 (m, 2H) 6.85 (m, 2H), 7.00 (m, 4H), 7.18 (m, 2H), 7.28 (m, 3H).

Workup

  1. customAfter the material was consumed
  2. concentrationthe solution was concentrated
  3. customto give residue, which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-1cf84b646e434d20aa02e478a7fec2e8
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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