HCID 23138651, compound → HCID 86609447, compound

HRID 1171701Notes

Reaction equation

HRID 1171701 reaction equation
[CH3:1][O:2][C:3]([CH2:5][N:6]1[C:10](/[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:9][CH:8]=[N:7]1)=[O:4].[CH3:38][O:39][C:40]([CH2:42][N:43]1[CH:47]=[N:46][C:45](/[CH:48]=[C:49]2\[CH2:50][N:51]([C:56]([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH2:52][CH2:53][CH:54]\2O)=[N:44]1)=[O:41].[C:75]([OH:78])(=[S:77])[CH3:76]>ClCCl.C1(C)C=CC=CC=1.C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>[C:75]([S:77][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:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:13]/[C:12]/1=[CH:11]\[C:10]1[N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[N:7]=[CH:8][N:9]=1)(=[O:78])[CH3:76].[C:75]([S:77][CH:54]1[CH2:53][CH2:52][N:51]([C:56]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[CH2:50]/[C:49]/1=[CH:48]\[C:45]1[N:46]=[CH:47][N:43]([CH2:42][C:40]([O:39][CH3:38])=[O:41])[N:44]=1)(=[O:78])[CH3:76]

Participants

8

Reactant 3

HCID 23138651HCID 23138651, compoundHCID 23138902HCID 23138902, compoundHCID 178418634HCID 178418634, compound

Product 2

HCID 86609446HCID 86609446, compoundYield 46%HCID 86609447HCID 86609447, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineSolvent

Procedure

The mixture (2.98 g) of (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol and (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol obtained in Example 166-(b) was dissolved in a mixed solvent of dichloromethane (40 ml) and toluene (40 ml), and thioacetic acid (1.3 ml) and N,N-dimethylformamide dineopentyl acetal (5.0 ml) were added thereto. After the mixture was stirred at room temperature for 2 hours, it was partitioned between water and ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure gave a residue, which was purified by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (1:1:1) to afford (E)-4-(acetylsulfanyl)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (containing impurities, 1.52 g, gross yield: 46%) as the less polar isomer, and (E)-4-(acetylsulfanyl)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-3-yl]methylidene}-1-(triphenylmethyl)piperidine (2.08 g, yield: 62%) as the polar isomer, respectively.

Workup

  1. additionwere added
  2. customit was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customgave a residue, which
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-421c574ddcbe45b4bf34e9e633d7e28d
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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