L-Isoleucine → HCID 67520545, compound

HRID 1925199Notes

Reaction equation

HRID 1925199 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[C:10](=O)([O:21]C1C=CC([N+]([O-])=O)=CC=1)[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>O1CCCC1>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4])=[O:21])=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 6306L-IsoleucineHCID 78756Bis(4-nitrophenyl) carbonate

Product 1

HCID 67520545HCID 67520545, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 300 ml round-bottomed flask equipped with a Dimroth condenser was charged with 13.13 g (100 mmol) of L-isoleucine and 1000 ml of tetrahydrofuran. After the addition of 30.4 g (100 mmol) of bis(4-nitrophenyl) carbonate, the mixture was stirred at 60° C. for 20 hours. After evaporating the solvent, the residue was purified by column chromatography to obtain 8.3 g of N-(4-nitrophenoxycarbonyl)-L-isoleucine.

Workup

  1. customA 300 ml round-bottomed flask equipped with a Dimroth condenser
  2. customAfter evaporating the solvent
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ee8f210c7ecb4d07a1f8572af3dfdc4c
Source dataset
uspto-grants-2012_05
Patent number
US08178641B2

Reaction notes

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