N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-isoleucine 2,3,4,5,6-pentafluorophenyl ester → N-Fmoc-L-isoleucine

HRID 916091Notes

Reaction equation

HRID 916091 reaction equation
[NH:1]([C:21]([O:23][CH2:24][CH:25]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[C@H:2]([C:7]([O:9]C1C(F)=C(F)C(F)=C(F)C=1F)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]>C1COCC1>[NH:1]([C:21]([O:23][CH2:24][CH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]2[C:37]1=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:22])[C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

3

Reactant 1

HCID 13585947N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-isoleucine 2,3,4,5,6-pentafluorophenyl ester

Product 1

HCID 2724629N-Fmoc-L-isoleucineYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of AE (50 mg; 0.185 mmol) in THF (5 ml) was added with Fmoc-L-Ile-OPfp (211 mg; 0.407 mmol). The solution was refluxed for 48 hrs, the solvent was evaporated, and the residue was purified by chromatography (petroleum ether/ethyl acetate 3:1). 42 mg (37%) of Fmoc-L-Ile-Aloe was isolated as an an orange-coloured powder.

Workup

  1. temperatureThe solution was refluxed for 48 hrs
  2. customthe solvent was evaporated
  3. customthe residue was purified by chromatography (petroleum ether/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-6f4bcb49de114f4ea605d89da2d58f9c
Source dataset
uspto-grants-2007_09
Patent number
US07268162B2

Reaction notes

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