Benzyl succinimido carbonate → HCID 14802498, compound

HRID 1602087Notes

Reaction equation

HRID 1602087 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[CH2:11]([O:18][C:19](ON1C(=O)CCC1=O)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[CH2:11]([O:18][C:19]([NH:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 14802498HCID 14802498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40.5 g (295 mmol) of (R)-2-amino-2-phenylethanol are dissolved in 385 ml of absolute dimethylformamide. 73.5 g of N-(benzyloxycarbonyloxy)succinimide (295 mmol) are added, at 0° C. and while stirring, and the mixture is then stirred at 0° C. for 1 hour. The ice bath is removed and the mixture is left to stand at room temperature for 48 h. The reaction solution is concentrated in vacuo and the residue is then taken up in 500 ml of ethyl acetate. The organic phase is washed twice with a 10% aqueous solution of citric acid and once with water. It is then dried over anhydrous sodium sulphate and concentrated. The resulting crystalline crude product (82.3 g) is once again dissolved in ethyl acetate. The organic phase is washed twice with a 10% aqueous solution of citric acid and once with water. Recrystallization subsequently takes place from ethyl acetate/petroleum ether.

Workup

  1. stirringthe mixture is then stirred at 0° C. for 1 hour
  2. customThe ice bath is removed
  3. waitthe mixture is left
  4. concentrationThe reaction solution is concentrated in vacuo
  5. washThe organic phase is washed twice with a 10% aqueous solution of citric acid and once with water
  6. dry with materialIt is then dried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. dissolutionThe resulting crystalline crude product (82.3 g) is once again dissolved in ethyl acetate
  9. washThe organic phase is washed twice with a 10% aqueous solution of citric acid and once with water
  10. customRecrystallization subsequently takes place from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-dca7bd92ad9147afa5d0b37e18caab37
Source dataset
uspto-grants-1999_11
Patent number
US05981492

Reaction notes

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