Trifluoroacetic acid → Caprine

HRID 893121Notes

Reaction equation

HRID 893121 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.C(OCC)C>[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 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

25.8 mg of the isomer having a high Rf value of L-N-[(2R or S)-5-ethylsulfonyl-2-(1-naphthylmethyl)pentanoyl]norleucine tert-butyl ester was dissolved in 0.2 ml of dichloromethane. Then, 0.1 ml of TFA was added thereto, and the mixture was stirred at room temperature for 4 hours. Then, the reaction solution was concentrated under reduced pressure. The residue thereby obtained was diluted with diethyl ether and concentrated under reduced pressure. This operation was repeated to obtain 22.9 mg of L-N-[(2R or S)-5-ethylsulfonyl-2-(1-naphthylmethyl)pentanoyl]norleucine.

Workup

  1. concentrationThen, the reaction solution was concentrated under reduced pressure
  2. customThe residue thereby obtained
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7dfd8fde6e64d9d8ef724291f03832d
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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