3,4-dihydro-2H-pyran → HCID 23368448, compound

HRID 1901621Notes

Reaction equation

HRID 1901621 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:24][OH:25])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([NH:21][CH:22]=[O:23])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:24][O:25][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][O:26]1)[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([NH:21][CH:22]=[O:23])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 86750032HCID 86750032, compound

Product 1

HCID 23368448HCID 23368448, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.45 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-formylamino-1,2-benzoisoxazole in 9 ml of methylene chloride are added 0.14 g of 3,4-dihydro-2H-pyran and 0.06 g of pyridinium p-toluenesulfonate at 20°-25° C., and they are subjected to reaction at 40° C. for one hour. Water is added to the reaction mixture and the pH is adjusted to 9 with a saturated aqueous sodium hydrogencarbonate solution, after which the organic layer is separated. The separated organic layer is dried over anhydrous magnesium sulfate, and the solvent is then removed by distillation under reduced pressure, to obtain oily 3-[2-tert-butoxycarbonylamino-3-(2,3,4,5-tetrahydropyranyloxy)propoxy]-5-formylamino-1,2-benzoisoxazole.

Workup

  1. customthey are subjected to reaction at 40° C. for one hour
  2. customafter which the organic layer is separated
  3. dry with materialThe separated organic layer is dried over anhydrous magnesium sulfate
  4. customthe solvent is then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-73b05ea0ece94785a9e23f8e33ce9e71
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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