Water → HCID 54017596, compound

HRID 486732Notes

Reaction equation

HRID 486732 reaction equation
[C:1]([S:4][CH2:5][C@H:6]1[CH2:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7]1)(=[O:3])[CH3:2].C(NC(C)C)(C)C.O.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[C:1]([S:4][CH2:5][C@H:6]1[CH2:10][C@H:9]([C:11]([O:13][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:12])[CH2:8][S:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 54063270HCID 54063270, compound

Product 1

HCID 54017596HCID 54017596, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of (2R,4R)-2-acetylthiomethyl-4-carboxytetrahydrothiophene (compound No. 13-2, 0.18 g) in dimethylformamide (4 ml), benzyl bromide dissolved in dimethylformamide (4 ml) and diisopropylamine (214 μl) were added and the mixture was stirred over night. Water was added to the mixture and extracted with diethylether. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.18 g (71%) of the titled compound (compound No. 14-1).

Workup

  1. extractionextracted with diethylether
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-22bf6f4e53a8404d87c41f5802e856c6
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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