Dimethyl Sulfide → HCID 57788115, compound

HRID 1690227Notes

Reaction equation

HRID 1690227 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:22]SC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:22])[C@H:9]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24758Sodium hydrideHCID 10967413HCID 10967413, compound

Product 1

HCID 57788115HCID 57788115, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To (R)-methyl 2-(tert-butoxycarbonylamino)-2-phenylacetate (E4) in DMF at −40° C. was added NaH and the solution was warmed to 0° C. for 20 minutes. DMS was added and solution was stirred at room temperature for 3 hours. The mixture was poured into NH4Cl(sat)/HCl (1N) 3:1 and extracted with EtOAc. The organics were dried (Na2SO4), filtered and evaporated to give crude E5. Column chromatography Hexanes/EtOAc gave pure (R)-methyl 2-(tert-butoxycarbonyl (methyl)amino)-2-phenylacetate (E5).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8c60509fff1a423d8622dfb549db892c
Source dataset
uspto-grants-2012_04
Patent number
US08153654B2

Reaction notes

Loading…