Potassium Carbonate → HCID 86622359, compound

HRID 501748Notes

Reaction equation

HRID 501748 reaction equation
Br[CH2:2][C@@H:3]([OH:25])[C@@H:4]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:13][C:8]1[CH:7]=[C:6]([CH2:5][C@H:4]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:3]2[CH2:2][O:25]2)[CH:11]=[C:10]([Cl:12])[CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86622360HCID 86622360, compound

Product 1

HCID 86622359HCID 86622359, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step BF (7): To a suspension of benzyl (2S,3S)-4-bromo-1-(3,5-dichlorophenyl)-3-hydroxybutan-2-ylcarbamate (100 mg, 224 umol) in MeOH (2.4 mL) was added K2CO3 (12 mg). The reaction was stirred vigorously overnight. Solvents were removed in vacuo, and the residue partitioned between EtOAc and water three times. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the solid benzyl (S)-2-(3,5-dichlorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate (78.9 mg, 97% yield). 1H NMR (DMSO-d6) δ 7.08-7.55 (m, 9H) 4.99 (d, J=12.8 Hz, 1H) 4.89 (d, J=12.8 Hz, 1H) 3.60-3.78 (m, 1H) 2.89-3.06 (m, 2H) 2.60-2.79 (m, 3H).

Workup

  1. customSolvents were removed in vacuo
  2. customthe residue partitioned between EtOAc and water three times
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e7abb4418574323abfba3442f894d8d
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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