تفاعل #310496

ord-97641a96c18a471692c4d73a6ed2f98c

معادلة التفاعل

O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1
benzyloxycarbonylproline
N=C(N)NCCC[C@H](N)C(=O)O
arginine
N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1)C(=O)O
Benzyloxycarbonyl-prolyl-arginine

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىTwo hours thereafter the solvent is evaporated
  2. 2
    workup.DISSOLUTIONthe precipitate is dissolved in 100 ml of dimethylformamide
  3. 3
    workup.ADDITIONpoured into 1 liter of ethylacetate
  4. 4
    غسيلwashed on the
  5. 5
    ترشيحfilter with ethylacetate
  6. 6
    أخرىreprecipitated from a mixture ethanol-ethylacetate

الإجراء التجريبي

To a solution of 37 g (0.1 mol) of p-nitrophenyl ester of benzyloxycarbonylproline in 360 ml of dioxane there is added a solution of 16 g (0.09 mol) of arginine in 160 ml of water under vigorous stirring. Two hours thereafter the solvent is evaporated and the precipitate is dissolved in 100 ml of dimethylformamide. The solution is stirred at room temperature for 72 hours and poured into 1 liter of ethylacetate. The resulting residue is filtered-off, washed on the filter with ethylacetate and reprecipitated from a mixture ethanol-ethylacetate. The yield of product (I) is 35 g (96%); the product has the following properties: M.p. 190° C., [α]D20 -46.6°; (c 1.0; H2O); Rf =0.53 (A, "Silufol") 0.66 (B, "Eastman"); EHis =0.56 (pH=2.4).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04353823uspto-grants-1982_10