1,2-Dibromoethane → methyl (3S)-2,2-dimethylthiomorpholine-3-carboxylate

HRID 2414647Notes

Reaction equation

HRID 2414647 reaction equation
Br[CH2:2][CH2:3]Br.Cl.[CH3:6][O:7][C:8](=[O:15])[C@@H:9]([C:11]([SH:14])([CH3:13])[CH3:12])[NH2:10].N12CCCN=C1CCCCC2.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:12][C:11]1([CH3:13])[S:14][CH2:3][CH2:2][NH:10][C@H:9]1[C:8]([O:7][CH3:6])=[O:15]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 12278508Methyl 3-mercapto-D-valinate hydrochloride

Product 1

HCID 18345630methyl (3S)-2,2-dimethylthiomorpholine-3-carboxylateYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 5.15 mL (59.8 mmol) of 1,2-dibromoethane in 50 mL of DMF at room temperature was added over 45 min a solution of 10 g (50 mmol) of D-penicillamine methyl ester hydrochloride and 22.5 mL (150.45 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 100 mL of DMF. The reaction was stirred for 2.5 h, poured into a solution of saturated NaHCO3 and extracted with ethyl acetate. The organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide 8.24 g (87%) of methyl (3S)-2,2-dimethyl-3-thiomorpholine carboxylate as a pale yellow oil. Electrospray Mass Spec: 190.1 (M+H)+

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed856af36a804309ad0c090a8df594de
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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