1,1'-Carbonyldiimidazole → HCID 54375516, compound

HRID 2289049Notes

Reaction equation

HRID 2289049 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][CH:35]1[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36]1>C(#N)C>[C:42]([O:41][C:39]([N:37]1[CH2:38][CH: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:40])([CH3:45])([CH3:43])[CH3:44]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 53836194HCID 53836194, compound

Product 1

HCID 54375516HCID 54375516, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1-(4-nitrobenzyloxycarbonyl)-L-proline (2.81 g) in anhydrous acetonitrile (40 ml), N,N-carbonyldiimidazole (1.42 g) was added at room temperature, followed by stirring for one hour. The reaction mixture was allowed to react under ice cooling with a solution of 3-amino-1-(tert-butoxycarbonyl)azetidine (1.31 g) in anhydrous acetonitrile (10 ml) in a similar manner to that described in Referential Example 1-(1), whereby 2.74 g of 1-(tert-butoxycarbonyl)-3-[1-(4-nitrobenzyloxycarbonyl)-L-prolylamino]azetidine were obtained.

Sources & evidence

ORD record
ord-e9d42e6fb87d4beaadee9b7bc5f3189d
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

Loading…