L-Phenylalanine → L-Leucine

HRID 2229869Notes

Reaction equation

HRID 2229869 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=CC=C[CH:5]=1>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C(Cl)Cl>[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH:4]([CH3:9])[CH3:5]

Participants

4

Reactant 1

HCID 6140L-Phenylalanine

Product 1

HCID 6106L-LeucineYield 222.7%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of compound (16) (211 mg, 0.64 mmol) and CH2Cl2 (20 mL) was purged with argon gas for 10 minutes. Grubbs Catalyst 1 (1.6 mg, 19.2 μmol) was added and the reaction was heated to reflux and monitored by TLC. The reaction was concentrated under reduced pressure and subjected to flash chromatography (2:1 Hexanes/EtOAc) to afford 187 mg (98%) of (17a) as a separable mixture of two diastereomers (17a, and 17a), both as colorless oils.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux
  3. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-247bc2ca1fec47b0a15bddeb42021df5
Source dataset
uspto-grants-2002_07
Patent number
US06420586B1

Reaction notes

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