Reaktion #1245805

ord-fd6aa1362c4943f6a58b061d0e26da48

Reaktionsgleichung

Cl.ONCc1ccccc1
N-benzylhydroxylamine hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CN(C)c1cc(NC(=O)CBr)c(O)c2c1CC1CC3C(N(C)C)C(O)=C(C(N)=O)C(=O)C3(O)C(O)=C1C2=O
9-(2-bromo-acetylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide
→
CN(C)c1cc(NC(=O)CN(O)Cc2ccccc2)c(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C2=O
product
Ausbeute 36.8%
CN(C)c1cc(NC(=O)CN(O)Cc2ccccc2)c(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C2=O
(4S,4aS,5aR,12aS)-9-[(N-benzyl-N-hydroxyglycyl)amino]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Ausbeute 36.8%

Edukte

Cl.ONCc1ccccc1
N-benzylhydroxylamine hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CN(C)c1cc(NC(=O)CBr)c(O)c2c1CC1CC3C(N(C)C)C(O)=C(C(N)=O)C(=O)C3(O)C(O)=C1C2=O
9-(2-bromo-acetylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

Reagenzien

Keine

Lösungsmittel

CN1CCCN(C)C1=O
DMPU
CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The compound of the example is prepared by the procedure of Example 1 using 3 g of N-benzylhydroxylamine hydrochloride, 2 g of sodium carbonate, and 0.8 g of 9-(2-bromo-acetylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide in 10 ml DMPU and 3 ml acetonitrile to give 0.315 g of the product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07812008B2uspto-grants-2010_10