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

HRID 905003Notes

Reaction equation

HRID 905003 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]([N:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[S:23]Cl)=[O:21])[CH3:18].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:17]([O:19][C:20]([N:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[S:23][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:21])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2566CarbofuranHCID 54484511N-ethoxycarbonyl-N-ethoxycarbonylmethylaminosulfenyl chloride

Product 1

HCID 3067963Glycine, (((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(ethoxycarbonyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.2 g (0.01 mole) of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl-carbamate, 2.4 g (0.01 mole) of N-ethoxycarbonyl-N-ethoxycarbonylmethylaminosulfenyl chloride obtained in Example 17, and 3.2 g (0.04 mole) of pyridine were dissolved in 30 ml of chloroform, and the resulting solution was stirred for 24 hours at 20° to 30° C. After completion of the reaction, the reaction solution was washed successively with water, diluted hydrochloric acid and water. The chloroform layer was dried and concentrated under reduced pressure to obtain an oily product which was almost entirely composed of the desired product although containing small amounts of the starting materials and impurities.

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 chloroform layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customto obtain an oily product which

Sources & evidence

ORD record
ord-7ba4be13ef85450e928186949f9b22c8
Source dataset
uspto-grants-1983_12
Patent number
US04421693

Reaction notes

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