Triethylamine → HCID 58109289, compound

HRID 2037553Notes

Reaction equation

HRID 2037553 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:24])([CH2:21][CH:22]=[CH2:23])[CH2:9][CH2:10][NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH3:13])=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:21]([C@@:8]1([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:24][C:33](=[O:35])[N:11]([C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH3:13])[CH2:10][CH2:9]1)[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 66857098HCID 66857098, compound

Product 1

HCID 58109289HCID 58109289, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-fluorophenyl)-1-((S)-1-(3-fluorophenyl)ethylamino)hex-5-en-3-ol (350 mg, 1.1 mmol) and Et3N (333 mg, 3.3 mmol) in anhydrous CH2Cl2 (6 mL) was added triphosgene (155 mg, 0.52 mmol) in portions at 0° C. under N2. Then the solution was refluxed overnight. After the solvent was removed under reduced pressure, the residue was purified by preparative TLC to afford (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(3-fluorophenyl)ethyl)-1,3-oxazinan-2-one (80 mg, 21%).

Workup

  1. temperatureThen the solution was refluxed overnight
  2. customAfter the solvent was removed under reduced pressure
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-e99d55122bda47f18251826239dff62d
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…