Reaktion #736006

Reaktionsgleichung

1-[N-[7-amino-3-(benzoylamino)-2-oxoheptyl]-L-alanyl]-L-proline, hydrochloride

1-[N-[3-(Benzoylamino)-7-[[(phenylmethoxy)carbonyl]amino]-2-oxoheptyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline

methanol

hydrochloric acid

→

1-[N-[7-Amino-3-(benzoylamino)-2-oxoheptyl]-L-alanyl]-L-proline, dihydrochloride

Lösungsmittel

ethanol

n-butanol acetic acid water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis hydrogenated at atmospheric pressure overnight
2. 2
   FiltrationThe catalyst is filtered off
3. 3
   Sonstigethe solution is evaporated in vacuo
4. 4
   workup.DISSOLUTIONThe residue is dissolved in water
5. 5
   SonstigeThe lyophilate is triturated with ether
6. 6
   Sonstigeto give 0.6 g

Vorschrift

1-[N-[3-(Benzoylamino)-7-[[(phenylmethoxy)carbonyl]amino]-2-oxoheptyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, phenylemethyl ester (1.3 g., 1.6 mmole) is dissolved in ethanol (75 ml.) and aqueous hydrochloric acid (1N, 5 ml.). Palladium on carbon catalyst (10%, 450 mg.) is added and the mixture is hydrogenated at atmospheric pressure overnight. The catalyst is filtered off and the solution is evaporated in vacuo. The residue is dissolved in water and lyophilized. The lyophilate is triturated with ether to give 0.6 g. of 1-[N-[7-amino-3-(benzoylamino)-2-oxoheptyl]-L-alanyl]-L-proline, hydrochloride; m.p. 80°-155°; [α]D22 =-50° (c=1.1, methanol). Rf 0.09 (silica gel, n-butanol/acetic acid/water, 4:1:1).

Quelle