Reaktion #5079

ord-e95bb68602144d5c8b548570c446fb1d

Reaktionsgleichung

CC(C)(C)OC(=O)NCC(=O)O
Boc-Gly-OH
CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1
H-Leu-Ala-OBzl
→
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

Edukte

—
anhydride
CC(C)(C)OC(=O)NCC(=O)O
Boc-Gly-OH
CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)OCc1ccccc1
H-Leu-Ala-OBzl

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

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