Water → HCID 67733418, compound

HRID 1901636Notes

Reaction equation

HRID 1901636 reaction equation
[H-].[Na+].[CH3:3][S:4][CH2:5][C@H:6]([NH:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][OH:8].Cl[C:30]1[C:34]2[CH:35]=[C:36]([Cl:39])[CH:37]=[CH:38][C:33]=2[O:32][N:31]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]2[O:32][N:31]=[C:30]([O:8][CH2:7][C@@H:6]([NH:9][C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][S:4][CH3:3])[C:34]=2[CH:35]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 135684483,5-Dichloro-1,2-benzoxazoleHCID 53842957HCID 53842957, compound

Product 1

HCID 67733418HCID 67733418, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 0.44 g of 60% (w/w) sodium hydride in 6 ml of N,N-dimethylformamide is dropwise added 15 ml of an N,N-dimethylformamide solution of 4.0 g of (R)-3-methylthio-2-tritylamino-1-propanol over 15 minutes with ice-cooling, and the temperature is gradually elevated to 80° C., after which this is added to a solution of 2.07 g of 3,5-dichloro-1,2-benzoisoxazole in 10 ml of N,N-dimethylformamide. They are subjected to reaction at the same temperature for one hour. After cooling, water and ethyl acetate are added and 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 column chromatography [eluant:n-hexane:ethyl acetate=20:1], to obtain 4.4 g of oily (R)-5-chloro-3-(3-methylthio-2-tritylaminopropoxy)-1,2-benzoisoxazole.

Workup

  1. customover 15 minutes
  2. temperaturecooling
  3. customis gradually elevated to 80° C.
  4. customThey are subjected to reaction at the same temperature for one hour
  5. temperatureAfter cooling
  6. customthe organic layer is separated
  7. washThe separated organic layer is washed with a saturated saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customafter which the solvent is removed by distillation under reduced pressure
  10. customThe residue obtained
  11. customis purified by a column chromatography [eluant:n-hexane:ethyl acetate=20:1]

Sources & evidence

ORD record
ord-e074c0fce7d649a0bec1ab4e095b58df
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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