Reaktion #5080

ord-1e9e6ea312024abbb5827b12a87dd34a

Reaktionsgleichung

CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1
Boc-Gly-Leu-Ala-OBzl
O=C(O)C(F)(F)F
trifluoroacetic acid
CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1
H-Leu-Ala-OBzl
O=C([O-])C(F)(F)F
trifluoroacetate
Cl
hydrogen chloride
→
CC(C)C[C@H](NC(=O)CN)C(=O)N[C@@H](C)C(=O)OCc1ccccc1.Cl
H-Gly-Leu-Ala-OBzl HCl

Edukte

CC(C)C[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)OCc1ccccc1
Boc-Gly-Leu-Ala-OBzl
O=C(O)C(F)(F)F
trifluoroacetic acid
CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1
H-Leu-Ala-OBzl
O=C([O-])C(F)(F)F
trifluoroacetate
Cl
hydrogen chloride

Reagenzien

Keine

Lösungsmittel

CCOCC
ether
CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe resulting product was precipitated by the addition of ether

Vorschrift

Boc-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Gly-OH (5.70 g, 32.6 mmoles) to H-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The product (13.8 g) was obtained as an amorphous solid. Boc-Gly-Leu-Ala-OBzl was deblocked with trifluoroacetic acid by the procedure described for the preparation of H-Leu-Ala-OBzl except that the trifluoroacetate salt was soluble in ether. The preparation was dissolved in ethyl acetate and treated with anhydrous hydrogen chloride. The resulting product was precipitated by the addition of ether to yield 7.7 g of H-Gly-Leu-Ala-OBzl HCl in a first crop.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05242904uspto-grants-1993_09