تفاعل #5080

ord-1e9e6ea312024abbb5827b12a87dd34a

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

CCOCC
ether
CCOC(C)=O
ethyl acetate

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05242904uspto-grants-1993_09