Reaktion #572368

Reaktionsgleichung

methanol

hydrochloric acid

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

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

→

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

Lösungsmittel

n-butanol acetic acid water

ethanol

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, phenylmethyl 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