Trifluoroacetic acid → Caprine

HRID 893139Notes

Reaction equation

HRID 893139 reaction equation
C([O:5][C:6](=[O:13])[C@H:7]([CH2:9][CH2:10][CH2:11][CH3:12])[NH2:8])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl.C1C=CC=CC=1>[NH2:8][C@H:7]([C:6]([OH:13])=[O:5])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12451446tert-butyl (2S)-2-aminohexanoate

Product 1

HCID 21236Caprine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

358 mg of the isomer having a high Rf value of L-N-[(2S or R)-2-ethylsulfonylmethyl-4-methylpentanoyl]norleucine tert-butyl ester was dissolved in dry dichloromethane, and 1.5 ml of TFA was added thereto. The reaction solution was stirred at room temperature for 1.5 hours, and then concentrated under reduced pressure to obtain a syrup. The syrup was dissolved in benzene, and the solution was concentrated under reduced pressure. This operation was repeated. The syrup was crystallized from diethyl ether/n-hexane, and evaporated under reduced pressure to dryness to obtain 312 mg of L-N-[(2S or R)-2-ethylsulfonylmethyl-4-methylpentanoyl]norleucine as colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto obtain a syrup
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe syrup was crystallized from diethyl ether/n-hexane
  5. customevaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-42fc276eb98242cea098612ba97d14b3
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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