Triethylamine → methyl N-t-butoxycarbonyl-S-[(3,4-methylenedioxy)phenyl]cysteinate

HRID 483804Notes

Reaction equation

HRID 483804 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([SH:10])=[CH:4][C:3]=2[O:2]1.[C:11]([O:15][C:16]([NH:18][C@H:19]([C:32]([O:34][CH3:35])=[O:33])[CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:11]([O:15][C:16]([NH:18][C@H:19]([C:32]([O:34][CH3:35])=[O:33])[CH2:20][S:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27598473,4-(Methylenedioxy)thiophenolHCID 7009424Boc-Ser(Tos)-OMe

Product 1

HCID 18652697methyl N-t-butoxycarbonyl-S-[(3,4-methylenedioxy)phenyl]cysteinateYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

After 27.7 g of (3,4-methylenedioxy)thiophenol and 74 g of methyl N-(t-butoxycarbonyl)-O-tosyl-L-serinate were dissolved in 200 ml of chloroform, 20 g of triethylamine were added at room temperature, followed by stirring overnight. The reaction mixture was washed with water and then extracted with ethyl acetate. The extract so obtained was dried over anhydrous magnesium sulfate. After the solvent was distilled off, 49 g of crude oil were obtained. The crude oil was recrystallized from an ethyl acetatehexane system, whereby 42 g of methyl N-t-butoxycarbonyl-S-[(3,4-methylenedioxy)phenyl]cysteinate were obtained (yield: 66%).

Workup

  1. washThe reaction mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. extractionThe extract so
  4. customobtained
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. custom49 g of crude oil were obtained
  8. customThe crude oil was recrystallized from an ethyl acetatehexane system

Sources & evidence

ORD record
ord-b7ea69842239425ca8143b0c5d4aa26f
Source dataset
uspto-grants-1993_07
Patent number
US05227398

Reaction notes

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