Sodium Carbonate → HCID 86641456, compound

HRID 1189971Notes

Reaction equation

HRID 1189971 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:10]=[C:11](/[CH:15]=[CH:16]/[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]1([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:15]3[O:34][CH:16]3[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86729711HCID 86729711, compound

Product 1

HCID 86641456HCID 86641456, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-tert-butyl 3-(3-(cyclohexylmethylamino)phenyl)allylcarbamate in CH2Cl2 is added MCPBA (77%) followed by Na2CO3. The reaction mixture is stirred at room temperature until no starting material is seen by TLC. Aqueous NaHCO3 (10%) is added and the product is extracted with CH2Cl2 three times. Combined organic layers are washed with brine-NaHCO3, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (10% to 50% EtOAc—hexanes gradient) gives tert-butyl (3-(3-(cyclohexylmethylamino)phenyl)oxiran-2-yl)methylcarbamate which is used in the next step without further purification.

Workup

  1. extractionthe product is extracted with CH2Cl2 three times
  2. washCombined organic layers are washed with brine-NaHCO3
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (10% to 50% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-9c17b839052c4fa9a76c5fc77d547d99
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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