1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 86609443, compound
Reaction equation
[CH3:1][O:2][C:3]([CH2:5][N:6]1[CH:10]=[C:9](/[CH:11]=[C:12]2\[CH2:13][N:14]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:16][CH:17]\2O)[N:8]=[N:7]1)=[O:4].[C:38]([OH:41])(=[S:40])[CH3:39].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>>[C:38]([S:40][CH:17]1[CH2:16][CH2:15][N:14]([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:13]/[C:12]/1=[CH:11]\[C:9]1[N:8]=[N:7][N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH:10]=1)(=[O:41])[CH3:39]Participants
Procedure
Following a procedure similar to that described in Example 160-(e), (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,3-triazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (4.7 g) was treated with thioacetic acid and N,N-dimethylformamide dineopentyl acetal. After extraction, the obtained substance was purified by silica gel chromatography to afford (E)-4-(acetylsulfanyl)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,3-triazol-4-yl]methylidene}-1-(triphenylmethyl)piperidine (2.6 g). This compound was similarly treated with trifluoroacetic acid in dichloromethane and the residue obtained by concentration of the reaction mixture was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.026 N aqueous trifluoroacetic acid solution, 18/82, v/v) to afford the title compound (550 mg, yield: 14%) as a yellow amorphous solid.
Workup
- extractionAfter extraction
- customthe obtained substance was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-0c9014903e1e4ec3aa55fdd52d45d559
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829580B2
Reaction notes
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