1,1'-Carbonyldiimidazole → HCID 57047864, compound

HRID 2289046Notes

Reaction equation

HRID 2289046 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:20]([OH:22])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[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:20](=[O:22])[C@@H:4]2[CH2:3][CH:2]([OH:1])[CH2:6][N:5]2[C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[O:8])[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 53963276HCID 53963276, compound

Product 1

HCID 57047864HCID 57047864, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline (1.79 g) in anhydrous acetonitrile (30 ml), N,N,-carbonyldiimidazole (981 mg) was added at room temperature, followed by stirring at room temperature for one hour. To the reaction mixture, a solution of (3S)-3-amino-1-(tert-butoxycarbonyl)pyrrolidine (1.02 g) in anhydrous acetonitrile (20 ml) was added under ice cooling. The resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was purified in a similar manner to that described in Referential Example 1-(1), whereby 1.22 g of (3S)-1-(tert-butoxycarbonyl)-3-[1-(4-nitrobenzyloxycarbonyl)-4-hydroxy-L-prolylamino]pyrrolidine were obtained as an amorphous substance.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 6 hours
  2. customThe reaction mixture was purified in a similar manner to that

Sources & evidence

ORD record
ord-c7f67cc635d448bb84834a6142fe793a
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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