Reaction equation
[CH:1]([N:4]([CH2:16][CH2:17][CH2:18][CH:19]=O)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[CH3:21][NH:22][CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[C:27]([O:28][CH3:29])[CH:26]=1>C(O)C.O=[Pt]=O>[Cl:15][C:10]1[CH:9]=[C:8]([S:5]([N:4]([CH2:16][CH2:17][CH2:18][CH2:19][N:22]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[C:27]([O:28][CH3:29])[CH:26]=2)[CH3:21])[CH:1]([CH3:2])[CH3:3])(=[O:6])=[O:7])[CH:13]=[CH:12][C:11]=1[Cl:14]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
The aldehyde prepared in the preceding paragraph (8.90 g, 0.027 m) and N-methyl-homoveratrylamine (5.29 g, 0.027 m) in absolute ethanol (100 ml) containing PtO2 (0.6 g) was shaken under hydrogen (7 hours) and the reaction filtered and stripped to provide the crude product (13.32 g) as a dark greenish gum. This material was chromatographed, after removal of a small amount of insoluble solid, on dry column silica gel (500 g) with 30% methanol/70% ethyl acetate to provide the title compound (7.26 g) as a clear white gum.
Workup
- filtrationthe reaction filtered
- customto provide the crude product (13.32 g) as a dark greenish gum
- customThis material was chromatographed
- customafter removal of a small amount of insoluble solid
- dry with materialon dry column silica gel (500 g) with 30% methanol/70% ethyl acetate
Sources & evidence
- ORD record
- ord-fe203a9032f446659f56f459b8ba90a1
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04618711
Linked notes
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