Triethylamine → HCID 23368380, compound

HRID 1901657Notes

Reaction equation

HRID 1901657 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].O1CCCC1.O.C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][N:28]=[C:27]([O:30][CH2:31][CH:32]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:33][OH:34])[C:26]=2[CH:43]=1>O1CCCC1.C(OCC)(=O)C.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][N:28]=[C:27]([O:30][CH2:31][CH:32]([NH:35][C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])[CH2:33][O:34][S:2](=[O:3])(=[O:4])[NH2:5])[C:26]=2[CH:43]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 21881883Oxolane--water (1/1)HCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 23368380HCID 23368380, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.378 ml of chlorosulfonyl isocyanate in 5 ml of tetrahydrofuran is dropwise added 0.78 ml of a tetrahydrofuran-water mixture (9:1 v/v) at -10° C. over five minutes, and the temperature is gradually elevated to 15° C. To this mixture are dropwise added at the same temperature 0.61 ml of triethylamine and a solution of 1.0 g of 5-chloro-3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-1,2-benzoisoxazole in 10 ml of tetrahydrofuran over ten minutes, after which they are subjected to reaction at room temperature for two hours. Water and ethyl acetate are added to the reaction mixture, they are shaken and 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. The residue obtained is purified by a silica gel column chromatography [eluant:toluene:ethyl acetate=5:1], to obtain 1.0 g of oily 5-chloro-3-(2-tert-butoxycarbonylamino-3-sulfamoyloxypropoxy)-1,2-benzoisoxazole.

Workup

  1. customat -10° C.
  2. customover five minutes
  3. customis gradually elevated to 15° C
  4. customafter which they are subjected to reaction at room temperature for two hours
  5. customthe organic layer is separated
  6. washThe separated organic layer is washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customafter which the solvent is removed by distillation under reduced pressure
  9. customThe residue obtained
  10. customis purified by a silica gel column chromatography [eluant:toluene:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-8fee94c73c9c4de2a25e2c0274247e19
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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