1,1'-Carbonyldiimidazole → HCID 70096333, compound

HRID 2289045Notes

Reaction equation

HRID 2289045 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([OH:16])=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:34][C@H:35]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]1>C(#N)C>[C:43]([O:42][C:40]([N:37]1[CH2:38][CH2:39][C@H:35]([NH:34][C:14](=[O:16])[C@@H:13]2[CH2:17][CH2:18][CH2:19][N:12]2[C:10]([O:9][CH2:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:21][CH:20]=2)=[O:11])[CH2:36]1)=[O:41])([CH3:46])([CH3:44])[CH3:45]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 53836194HCID 53836194, compound

Product 1

HCID 70096333HCID 70096333, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1-(4-nitrobenzyloxycarbonyl)-L-proline (3.67 g) in anhydrous acetonitrile (50 ml), N,N-carbonyldiimidazole (1.86 g) was added at room temperature. After stirring for one hour, a solution of (3S)-3-amino-1(tert-butoxycarbonyl)pyrrolidine (1.86 g) in anhydrous acetonitrile (20 ml) was added to the reaction mixture under ice cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was then concentrated by evaporation under reduced pressure. To the residue, ethyl acetate was added. The resulting mixture was washed with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column (ethyl acetate:dichloromethane=1:1), whereby 3.31 g of (3S)-1-(tert-butoxycarbonyl)-3-[1-(4-nitrobenzyloxycarbonyl)-L-prolylamino]pyrrolidine were obtained as a colorless amorphous substance.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  3. additionTo the residue, ethyl acetate was added
  4. washThe resulting mixture was washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by chromatography through a silica gel column (ethyl acetate:dichloromethane=1:1)

Sources & evidence

ORD record
ord-e23767c15eb94a6f840bc666c9ac96b7
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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