N,N-Dimethylglycine → HCID 58109630, compound

HRID 2037513Notes

Reaction equation

HRID 2037513 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[O:12][C:11]2=[O:33])[CH3:9])=[CH:4][CH:3]=1.[CH3:34][S:35]([NH2:38])(=[O:37])=[O:36].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C)CC(O)=O>CN(C=O)C.CCOC(C)=O.[Cu]I>[Si:26]([O:25][CH2:24][CH2:23][C@@:13]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:12][C:11](=[O:33])[N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:38][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:3][CH:4]=2)[CH3:9])[CH2:15][CH2:14]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 62657Potassium Phosphate, TribasicHCID 72879MethanesulfonamideHCID 58109139HCID 58109139, compound

Product 1

HCID 58109630HCID 58109630, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (0.0465 g, 0.0866 mmol), methanesulfonamide (0.0945 g), K3PO4 (0.2753 g), N,N-dimethylglycine (0.0686 g), and CuI (0.0687 g) in DMF (2 mL) was heated at 120° C. for 17 h. The mixture was diluted with EtOAc, filtered, washed with CH2Cl2. After the solvent was evaporated under reduced pressure, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford N-(4-((S)-1-((S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)phenyl)methanesulfonamide. LC-MS tR=2.10 min in 3 min chromatography, m/z 551 (MH+), 507.

Workup

  1. filtrationfiltered
  2. washwashed with CH2Cl2
  3. customAfter the solvent was evaporated under reduced pressure
  4. customthe residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%
  5. customover 8 min

Sources & evidence

ORD record
ord-34024587ea774452b17477b2dade5cb4
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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