Ethanolamine → HCID 58109728, compound

HRID 2037468Notes

Reaction equation

HRID 2037468 reaction equation
CS(O[CH2:6][CH2:7][C@@:8]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:19][CH:18]=2)[CH3:16])[CH2:10][CH2:9]1)(=O)=O.[NH2:38][CH2:39][CH2:40][OH:41]>CO>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[C:20]1[CH:21]=[CH:22][C:17]([C@@H:15]([N:11]2[CH2:10][CH2:9][C@@:8]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)([CH2:7][CH2:6][NH:38][CH2:39][CH2:40][OH:41])[O:13][C:12]2=[O:14])[CH3:16])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86649947HCID 86649947, compound

Product 1

HCID 58109728HCID 58109728, compoundYield 3.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-((S)-3-((S)-1-(2′,4′-difluorobi-phenyl-4-yl)ethyl)-6-(4-fluorophenyl)2-oxo 1,3-oxazinan-6-yl)ethyl methanesulfonate (58 mg, 0.11 mmol) in anhydrous MeOH was added 2-amino-ethanol (54 mg, 0.88 mmol). Then the reaction mixture was refluxed overnight. When the reaction was over, solvent was removed in vacuo. The residue was purified by preparative HPLC to give (R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-(2-hydroxyethylamino)ethyl)-1,3-oxazinan-2-one (2 mg, 3%). 1H NMR (CDCl3): 1.53 (m, 3H), 2.25-2.36 (m, 4H), 2.51 (m, 1H), 2.87-3.24 (m, 5H), 3.75-4.02 (m, 2H), 5.60 (m, 1H), 6.85-6.96 (m, 2H), 6.96-7.10 (m, 4H), 7.22 (m, 2H), 7.38 (m, 4H).

Workup

  1. temperatureThen the reaction mixture was refluxed overnight
  2. customwas removed in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-fa74a4ec76744f01955af90c8042d722
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…