1,1'-Carbonyldiimidazole → Carbonyldiimidazole boc-phenylalanine

HRID 2259979Notes

Reaction equation

HRID 2259979 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[C:13]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>C1COCC1>[C:13]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14].[C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)=[O:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 86759214Carbonyldiimidazole boc-phenylalanine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an argon atmosphere and under anhydrous conditions, 2.42 moles (391.8 g) of 1,1'-carbonyldiimidazole (CDI) and 3 liters of dry THF were mixed in a reactor. 1.89 moles (502.3 g) of Boc-phenylalanine was then added in five portions to the reactor to form a carbonyldiimidazole Boc-phenylalanine solution. Vigorous gas evolution was observed from the reaction. The mixture was refluxed for one hour and subsequently cooled to about 30° C.

Sources & evidence

ORD record
ord-dfb53cf5999942f989a5b5419a7de529
Source dataset
uspto-grants-1995_12
Patent number
US05475138

Reaction notes

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