Cyclopropylamine → HCID 71248777, compound

HRID 1019826Notes

Reaction equation

HRID 1019826 reaction equation
CS(O[CH2:6][C@@H:7]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH3:8])(=O)=O.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>>[CH:20]1([NH:23][CH2:6][C@@H:7]([NH:9][C:10](=[O:11])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:8])[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 10493514HCID 10493514, compound

Product 1

HCID 71248777HCID 71248777, compoundYield 60%

Procedure

(S)-2-(Benzyloxycarbonylamino)propyl methanesulfonate (48 mmol) and cyclopropyl amine (480 mmol) were mixed together and stirred at room temperature for 48 h. The remaining cyclopropyl amine was removed by rotary evaporator and the residual mixture was added to 500 ml of ethyl acetate and washed with 5% Na2CO3 aqueous solution and brine. After drying (K2CO3) and removal of the solvent, the residual semi-solid was recrystallized from CH2Cl2 and petroleum ether to afford the target compound in 60% yield.

Workup

  1. customThe remaining cyclopropyl amine was removed by rotary evaporator
  2. additionthe residual mixture was added to 500 ml of ethyl acetate
  3. washwashed with 5% Na2CO3 aqueous solution and brine
  4. customAfter drying
  5. custom(K2CO3) and removal of the solvent
  6. customthe residual semi-solid was recrystallized from CH2Cl2 and petroleum ether
  7. customto afford the target compound in 60% yield

Sources & evidence

ORD record
ord-661f6ee3d2ec4fcab2c454d7040f7995
Source dataset
uspto-grants-2014_05
Patent number
US08716293B2

Reaction notes

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