Pyridine → Glycine, N-(((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(2-ethoxy-2-oxoethyl)-, ethyl ester

HRID 905000Notes

Reaction equation

HRID 905000 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH2:17]([O:19][C:20]([CH2:22][N:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[S:24]Cl)=[O:21])[CH3:18].N1C=CC=CC=1>C(Cl)Cl>[CH2:30]([O:29][C:27]([CH2:26][N:23]([CH2:22][C:20]([O:19][CH2:17][CH3:18])=[O:21])[S:24][N:2]([CH3:1])[C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2566CarbofuranHCID 13135109Bis(ethoxycarbonylmethyl)aminosulfenyl Chloride

Product 1

HCID 3067956Glycine, N-(((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(2-ethoxy-2-oxoethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.4 g (0.02 mole) of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl-carbamate, 5.1 g (0.02 mole) of bis(ethoxycarbonylmethyl)aminosulfenyl chloride obtained in Example 1 or 2, and 4.7 g (0.06 mole) of pyridine were dissolved in 35 ml of methylene chloride, and the resulting solution was stirred for 30 hours at 30° to 35° C. After completion of the reaction, the reaction solution was washed successively with water, diluted hydrochloric acid and water. The methylene chloride layer was dried over sodium sulfate and concentrated under reduced pressure to obtain an oily product. Yield: 7.5 g (85.2%).

Workup

  1. customAfter completion of the reaction
  2. washthe reaction solution was washed successively with water, diluted hydrochloric acid and water
  3. dry with materialThe methylene chloride layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain an oily product

Sources & evidence

ORD record
ord-ed59f4c25a944ad987018f0b6d3629c5
Source dataset
uspto-grants-1983_12
Patent number
US04421693

Reaction notes

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