Benzaldehyde → 9-Amino-19-benzyl-14,32-dichloro-5-methyl-26-oxa-4-thia-3,8,10,16,19-pentaazatetracyclo[25.2.2.212,15.02,6] tritriaconta-1(29),2,5,8,12,14,23,27,30,32-decaene-7,17-dione

HRID 14411

Reaktionsgleichung

Reaktionsgleichung von HRID 14411
[NH2:1][C:2]1[NH:30][CH2:29][C:28]2[CH:31]=[C:32]([Cl:33])[C:25](=[C:26]([Cl:34])[CH:27]=2)[NH:24][C:23](=[O:35])[CH2:22][NH:21][CH2:20][CH2:19][CH2:18][CH:17]=[CH:16][CH2:15][O:14][C:13]2[CH:36]=[CH:37][C:10](=[CH:11][CH:12]=2)[C:9]2[C:5](=[C:6]([CH3:38])[S:7][N:8]=2)[C:4](=[O:39])[N:3]=1.[CH:40](=O)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OC)(OC)OC>C(O)(=O)C>[NH2:1][C:2]1[NH:30][CH2:29][C:28]2[CH:27]=[C:26]([Cl:34])[C:25](=[C:32]([Cl:33])[CH:31]=2)[NH:24][C:23](=[O:35])[CH2:22][N:21]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16][CH2:15][O:14][C:13]2[CH:12]=[CH:11][C:10](=[CH:37][CH:36]=2)[C:9]2[C:5](=[C:6]([CH3:38])[S:7][N:8]=2)[C:4](=[O:39])[N:3]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 1784351489-Amino-14,32-dichloro-5-methyl-26-oxa-4-thia-3,8,10,16,19-pentaazatetracyclo[25.2.2.212,15.02,6]tritriaconta-1(29),2,5,8,12,14,23,27,30,32-decaene-7,17-dione

Produkt 1

HCID 1784351479-Amino-19-benzyl-14,32-dichloro-5-methyl-26-oxa-4-thia-3,8,10,16,19-pentaazatetracyclo[25.2.2.212,15.02,6] tritriaconta-1(29),2,5,8,12,14,23,27,30,32-decaene-7,17-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

The cis/trans mixture of the title compound of 9-amino-14,32-dichloro-5-methyl-26-oxa-4-thia-3,8,10,16,19-pentaazatetracyclo[25.2.2.212,15.02,6]tritriaconta-1(29),2,5,8,12,14,23,27,30,32-decaene-7,17-dione (Example 4) (60 mg), benzaldehyde (24 mg), sodium triacetoxyborohydride (30 mg), trimethyl orthoformate (0.2 mL) and acetic acid (0.1 mL), in 2 mL of DMF was stirred at room temperature for 16 hrs. Ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL) were added. Layers were separated after the mixture was well shaken. The organic layer was dried over anhydrous magnesium sulfate and solvent was evaporated in vacuo to give a crude product, which was purified by preparative HPLC to give 27 mg of the title compound as an inseparable mixture of cis/trans isomers.

Quellen und Nachweise

ORD-Eintrag
ord-8585272f986b43429b57b80fb10e19a7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732434B2

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