Acetate → HCID 72707772, compound

HRID 541111Notes

Reaction equation

HRID 541111 reaction equation
C1([C@H:7]([N@:9]2[CH2:11][CH:10]2[C@H:12]([O:31][CH2:32]C2C=CC=CC=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:8])C=CC=CC=1.[CH3:39][C:40](O)=O.[C:43]([O-])(=O)[CH3:44].[OH-:47].[K+].[CH3:49][CH2:50]O>C(Cl)Cl>[CH2:32]([O:31][C@H:12]([C@@H:13]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:14][O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@H:10]([NH:9][C@@H:7]([C:40]1[CH:39]=[CH:44][CH:43]=[CH:50][CH:49]=1)[CH3:8])[CH2:11][OH:47])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 175AcetateHCID 176Acetic AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 178461669HCID 178461669, compound

Product 1

HCID 72707772HCID 72707772, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (R)-1-((R)-1-phenylethyl)-2-((1S,2S)-1,2,3-tris(benzyloxy)propyl)aziridine (340 mg, 0.67 mmol) in CH2Cl2 (2 mL, 0.3 M) was added AcOH (0.38 mL, 6.7 mmol, 10 equiv). The reaction mixture was stirred for 18 hrs at room temperature, diluted with CH2Cl2 and quenched with saturated NaHCO3 solution. The aqueous layer was extracted with CH2Cl2 and the combined organic layer was washed with brine, dried over MgSO4, filtered through a pad of celite and concentrated in vacuo. The resulting acetate was used without further purification. To a solution of the acetate in EtOH (2 mL, 0.3 M) was added KOH (113 mg, 2.1 mmol, 3 equiv). The reaction mixture was stirred for 2 hrs at room temperature, diluted with CH2Cl2 and quenched with water. The aqueous layer was extracted with CH2Cl2 and the combined organic layer was washed with brine, dried over MgSO4, filtered through a pad of celite and concentrated in vacuo. The resulting crude product was purified by silica gel flash chromatography with ethyl acetate/hexane (1/4 to 1/2) to afford the title product. Yield: 225 mg (64% yield over 2 steps); yellow oil.

Workup

  1. customquenched with saturated NaHCO3 solution
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad of celite
  6. concentrationconcentrated in vacuo
  7. customThe resulting acetate was used without further purification
  8. stirringThe reaction mixture was stirred for 2 hrs at room temperature
  9. customquenched with water
  10. extractionThe aqueous layer was extracted with CH2Cl2
  11. washthe combined organic layer was washed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered through a pad of celite
  14. concentrationconcentrated in vacuo
  15. customThe resulting crude product was purified by silica gel flash chromatography with ethyl acetate/hexane (1/4 to 1/2)

Sources & evidence

ORD record
ord-6d49b6e3a9954b34b2b20d1c59a70889
Source dataset
uspto-grants-2014_10
Patent number
US08871950B1

Reaction notes

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