Iodine → L-Leucine

HRID 1606826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606826
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([O:9]N1C(=O)CCC1=O)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(O)(C(F)(F)F)=O.CO.II>CN(C=O)C.CCN(CC)CC>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Komponenten

7

Edukt 4

HCID 807IodineHCID 887MethanolHCID 6422Trifluoroacetic acidHCID 11089751N-[(Phenylmethoxy)carbonyl]-L-leucine 2,5-dioxo-1-pyrrolidinyl ester

Produkt 1

HCID 6106L-Leucine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Z-Leu-OSu (LXIII) (10.8 gm), and the above TFA salt (LXIV) (17.8 gm) in DMF (200 mg) and Et3N (8.4 ml), were stirred at room temperature for 24 hours. The reaction mixture was evaporated in vacuo and the resulting peptide was partitioned between H2O and CHCl3. The dried (Na2SO4) organic layer was evaporated and crystallized from acetone-MeOH to afford 17.7 gm (80%) of pure LXV: m.p. 138°-140°C; [α]D22 -35.4 (c, 1.16, MeOH); Rf1 0.86 and Rf3 0.68, single spot with I2 reagent. Amino acid analysis gave Leu 1.1; Arg 0.9; Pro 1.0; Gly 1.0; NH3 0.9.

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe resulting peptide was partitioned between H2O and CHCl3
  3. dry with materialThe dried (Na2SO4) organic layer
  4. customwas evaporated
  5. customcrystallized from acetone-MeOH
  6. customto afford 17.7 gm (80%) of pure LXV

Quellen und Nachweise

ORD-Eintrag
ord-3a08098f79d9417c85401e9cea21e768
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03953416

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