Diphosgene → HCID 23368411, compound

HRID 1901606Notes

Reaction equation

HRID 1901606 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][OH:23])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:25](OC(Cl)(Cl)Cl)=[O:26].Cl.[CH3:33][O:34][NH2:35].C[O-].[Na+]>C(Cl)Cl.CO.O.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][O:23][C:25]([NH:35][O:34][CH3:33])=[O:26])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 10426DiphosgeneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 23368411HCID 23368411, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 1.00 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole and 0.73 g of triethylamine in 5 ml of methylene chloride is added to a solution of 0.42 g of trichloromethyl chloroformate in 5 ml of methylene chloride at 5°-7° C. over 20 minutes, and they are subjected to reaction at the same temperature for 30 minutes. This solution is added to a solution of 1.20 g of methoxyamine hydrochloride and 0.78 g of sodium methoxide in 15 ml of methanol at -30° C. and the temperature is elevated to 0° C., at which they are subjected to reaction for 30 minutes. Water is added to the reaction mixture, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure to obtain 3-(2-tert-butoxycarbonylamino-3-methoxyaminocarbonyloxypropoxy)-5-chloro-1,2-benzoisoxazole.

Workup

  1. customthey are subjected to reaction at the same temperature for 30 minutes
  2. customis elevated to 0° C., at which they
  3. customare subjected to reaction for 30 minutes
  4. customthe organic layer is separated
  5. washThe separated organic layer is washed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-df896198371b4813ba46ae7695f190de
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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