Triethylamine → HCID 58109609, compound

HRID 2037570Notes

Reaction equation

HRID 2037570 reaction equation
[CH:1]1([C@@H:7]([N:9]2[CH2:14][CH2:13][C@@:12]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([CH2:15][CH2:16][CH2:17][OH:18])[O:11][C:10]2=[O:26])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([O:18][CH2:17][CH2:16][CH2:15][C@@:12]1([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[O:11][C:10](=[O:26])[N:9]([C@H:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH3:8])[CH2:14][CH2:13]1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58109230HCID 58109230, compound

Product 1

HCID 58109609HCID 58109609, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-((S)-1-cyclohexylethyl)-6-(4-fluorophenyl)-6-(3-hydroxy propyl)-1,3-oxazinan-2-one (200 mg, 0.55 mmol) in CH2Cl2 (10 mL) was added Et3N (290 mg, 2.87 mmol) and MsCl (196 mg, 1.72 mmol) at 0° C. The reaction solution was stirred at rt for 2 h. The reaction was quenched by H2O and extracted with CH2Cl2. The organic phase was concentrated to give the 3-((R)-3-((S)-1-cyclohexylethyl)-6-(4-fluorophen-yl)-2-oxo-1,3-oxazinan-6-yl)propyl methanesulfonate (240 mg, 92%).

Workup

  1. customThe reaction was quenched by H2O
  2. extractionextracted with CH2Cl2
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-baae95312fdf4576b2b22fa24d83ab50
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…