Hydrochloric Acid → HCID 131713676, Verbindung

HRID 485186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485186
[C:1]([NH:9][CH:10]([CH2:44][CH2:45][CH2:46][CH2:47][NH:48]C(OCC1C=CC=CC=1)=O)[C:11](=[O:43])[CH2:12][N:13](C(OCC1C=CC=CC=1)=O)[C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([O:22]CC1C=CC=CC=1)=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:59].Cl.NCCCCC(NC(=O)C1C=CC=CC=1)C(=O)CN[C@H](C(N1CCC[C@H]1C(O)=O)=O)C.CO>C(O)C.[Pd].C(O)CCC.C(O)(=O)C.O>[ClH:59].[ClH:59].[NH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11](=[O:43])[CH2:12][NH:13][C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131713677HCID 131713677, VerbindungHCID 131713678HCID 131713678, Verbindung

Produkt 1

HCID 131713676HCID 131713676, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 22056973Butanol acetic acid waterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customis hydrogenated at atmospheric pressure overnight
  2. filtrationThe catalyst is filtered off
  3. customthe solution is evaporated in vacuo
  4. dissolutionThe residue is dissolved in water
  5. customThe lyophilate is triturated with ether
  6. customto give 0.6 g

Quellen und Nachweise

ORD-Eintrag
ord-638d9cfd098841df9ea8045a7fa638a4
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04535176

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