Hydrochloric Acid → HCID 23368408, compound

HRID 1901622Notes

Reaction equation

HRID 1901622 reaction equation
C(OC([NH:8][CH:9]([CH2:24][O:25]C1CCCCO1)[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([NH:21][CH:22]=O)[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.B#B.O.Cl>O1CCCC1>[NH2:8][CH:9]([CH2:24][OH:25])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([NH:21][CH3:22])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6328200DiboronHCID 23368448HCID 23368448, compound

Product 1

HCID 23368408HCID 23368408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-[2-tert-Butoxycarbonylamino-3-(2,3,4,5-tetrahydropyranyloxy)propoxy]-5-formylamino-1,2-benzoisoxazole is dissolved in 9 ml of tetrahydrofuran, and at 5°-10° C., 3.2 ml of a tetrahydrofuran solution (1M) of diborane is added, after which they are subjected to reaction at 20°-25° C. for one hour. Subsequently, 9 ml of water is added and the pH is adjusted to 0 with 6N hydrochloric acid, after which they are subjected to reaction at 20°-25° C. for one hour. The reaction mixture is concentrated under reduced pressure, ethyl acetate is added, and, after shaking, the aqueous layer is separated. Ethyl acetate is added again to the separated aqueous layer and the pH is adjusted to 11 with potassium carbonate, after which 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 0.22 g of brown, oily 3-(2-amino-3-hydroxypropoxy)-5-methylamino-1,2-benzoisoxazole.

Workup

  1. customafter which they are subjected to reaction at 20°-25° C. for one hour
  2. customafter which they are subjected to reaction at 20°-25° C. for one hour
  3. concentrationThe reaction mixture is concentrated under reduced pressure, ethyl acetate
  4. additionis added
  5. customthe aqueous layer is separated
  6. additionEthyl acetate is added again to the separated aqueous layer
  7. customafter which the organic layer is separated
  8. washThe separated organic layer is washed with a saturated saline solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customafter which the solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-13f12be194574b40ab9c097ae12c9e67
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

Loading…