p-Toluenesulfonic acid → (S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

HRID 1463035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463035
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([OH:20])=O)[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[S:21]1[C:25]2([CH2:29][C@@H:28]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[NH:27][CH2:26]2)[S:24][CH2:23][CH2:22]1.CC1C=CC(S(O)(=O)=O)=CC=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]([CH3:17])[C:18]([N:27]1[C@H:28]([C:30]([O:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:29][C:25]2([S:21][CH2:22][CH2:23][S:24]2)[CH2:26]1)=[O:20])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 199401P,P-Diphenylphosphinic azideHCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanineHCID 86739577(S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

Produkt 1

HCID 86739578(S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a cold (0°) solution of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine (720 mg., 2.57 mmole) and (S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester, p-toluenesulfonate (1.06 g., 1.1 eq.) in 8 ml. of dry dimethylformamide under argon is added dropwise a solution of 0.61 ml. (1.1 eq.) of diphenylphosphoryl azide in 1 ml. of dimethylformamide. The reaction mixture is worked up according to the procedure of Example 95(f) to yield (S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester.

Quellen und Nachweise

ORD-Eintrag
ord-09b76f000711465d93428ced3c2b97af
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04462943

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