Benzyl succinimido carbonate → HCID 14802498, compound

HRID 2184996Notes

Reaction equation

HRID 2184996 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=O)C>[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 mol) of (R)-2-amino-2-phenylethanol were dissolved in 385 ml of absolute DMF. 73.5 g of N-(benzyloxycarbonyloxy)succinimide (295 mmol) were added at 0° C. with stirring and the mixture was stirred at 0° C. for 1 hour. The ice bath was removed and the batch was allowed to stand at room temperature for 48 hours. The reaction solution was concentrated in vacuo and the residue was then taken up in 500 ml of ethyl acetate. The organic phase was washed twice with 10% strength aqueous citric acid solution and once with water. It was dried over anhydrous sodium sulfate and concentrated. The crystalline crude product obtained (82.3 g) was dissolved again in ethyl acetate. The organic phase was washed twice with 10% strength aqueous citric acid solution and once with water and concentrated. The residue was then recrystallized from ethyl acetate/petroleum ether. Yield: 74.6 g (93.3%).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. customThe ice bath was removed
  3. concentrationThe reaction solution was concentrated in vacuo
  4. washThe organic phase was washed twice with 10% strength aqueous citric acid solution and once with water
  5. dry with materialIt was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7cb44c84f69d46a39d6889459ce5f77e
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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