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

HRID 1180549Notes

Reaction equation

HRID 1180549 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].C(=O)(O)[O-].[Na+]>CN(C)C=O>[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

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 516892Sodium BicarbonateHCID 12278508Methyl 3-mercapto-D-valinate hydrochloride

Product 1

HCID 18345630methyl (3S)-2,2-dimethylthiomorpholine-3-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,2-dibromoethane (6.77 g, 36 mmol) in dimethylformamide (25 ml) was added, over a period of 30 minutes, a solution of D-penicillamine methyl ester hydrochloride (6 g, 30 mmol) and 1,8-diazobicyclo[5.4.0]undeca-7-ene (13.7 g, 90 mmol) in dimethylformamide (50 ml). The resulting mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into a saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed in vacuo to give 5.5 g (97%) of the product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bdc60ec671bf4b129201bb477950fc48
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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