1,1'-Carbonyldiimidazole → HCID 57040603, compound

HRID 2289048Notes

Reaction equation

HRID 2289048 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[C:18]([OH:20])=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:35][C@H:36]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37]1>C(#N)C>[C:44]([O:43][C:41]([N:38]1[CH2:39][CH2:40][C@H:36]([NH:35][C:18]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][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:22][CH:21]=2)=[O:11])=[O:20])[CH2:37]1)=[O:42])([CH3:47])([CH3:45])[CH3:46]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 105428031-{[(4-Nitrophenyl)methoxy]carbonyl}piperidine-2-carboxylic acid

Product 1

HCID 57040603HCID 57040603, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1-(4-nitrobenzyloxycarbonyl)-2-piperidinecarboxylic acid (1.54 g) in anhydrous acetonitrile (30 ml), N,N-carbonyldiimidazole (851 mg) was added at the room temperature, followed by stirring for one hour. The reaction mixture was allowed to react with a solution of (3S)-3-amino-1-(tert-butoxycarbonyl)pyrrolidine (931 mg) in anhydrous acetonitrile (15 ml) under ice cooling in a similar manner to that described in Referential Example 1-(1), whereby 1.81 g of (3S)-1-(tert-butoxycarbonyl)-3-[1-(4-nitrobenzyloxycarbonyl)piperidin-2-ylcarbonylamino]pyrrolidine were obtained as a colorless amorphous substance.

Sources & evidence

ORD record
ord-39a1d75dcba947949e321653cc4612ca
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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