Acetic-formic anhydride → HCID 86750032, compound

HRID 1901620Notes

Reaction equation

HRID 1901620 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][OH:14])[C:6]=2[CH:23]=1.[CH:24](OC(=O)C)=[O:25]>C(Cl)Cl>[C:19]([O:18][C:16]([NH:15][CH:12]([CH2:13][OH:14])[CH2:11][O:10][C:7]1[C:6]2[CH:23]=[C:2]([NH:1][CH:24]=[O:25])[CH:3]=[CH:4][C:5]=2[O:9][N:8]=1)=[O:17])([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 23368500HCID 23368500, compound

Product 1

HCID 86750032HCID 86750032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.59 g of 5-amino-3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-1,2-benzoisoxazole in 12 ml of methylene chloride is added 0.17 g of acetic formic anhydride at 5°-10° C., and they are subjected to reaction at 20°-25° C. for one hour. The solvent is removed from the reaction mixture by distillation under reduced pressure, and the residue obtained is crystallized from n-hexane, after which the crystals are collected by filtration, to obtain 0.52 g of colorless, crystalline 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-formylamino-1,2-benzoisoxazole having a melting point of 104°-105° C.

Workup

  1. customthey are subjected to reaction at 20°-25° C. for one hour
  2. customThe solvent is removed from the reaction mixture by distillation under reduced pressure
  3. customthe residue obtained
  4. customis crystallized from n-hexane
  5. filtrationafter which the crystals are collected by filtration

Sources & evidence

ORD record
ord-89253dd365b842ffb2c749ec9603dc85
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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