Imidazole → HCID 18391463, compound

HRID 1585807Notes

Reaction equation

HRID 1585807 reaction equation
N1C=CN=C1.[NH:6]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:7]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([NH2:18])=O)=[O:13])[C@H:8]([CH2:10][CH3:11])[CH3:9].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:16]([C@@H:15]1[CH2:19][CH2:20][CH2:21][N:14]1[C:12](=[O:13])[C@H:7]([C@H:8]([CH2:10][CH3:11])[CH3:9])[NH:6][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])#[N:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24813Phosphorus oxychlorideHCID 7124132HCID 7124132, compound

Product 1

HCID 18391463HCID 18391463, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Imidazole (84 mg, 1.24 mmol) was added to a solution of BocIleProNH2 in dry pyridine (10 cm3), under a nitrogen atmosphere. The solution was cooled to -35° C., before the dropwise addition of POCl3 (0.25 cm3, 2.48 mmol). The reaction was stirred at -30° C. to -20° C. for 60 min. The solution was then evaporated and the crude residue subjected to column chromatography (silica gel) to yield 180 mg (94%) of 2-(S)-cyano-1-[N-(t-butoxycarbonyl)isoleucyl]pyrrolidine as a colourless oil.

Workup

  1. customThe solution was then evaporated

Sources & evidence

ORD record
ord-68a817a467b943e183c334483b321c71
Source dataset
uspto-grants-1999_08
Patent number
US05939560

Reaction notes

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