Trifluoroacetic acid → HCID 87565843, compound

HRID 1171688Notes

Reaction equation

HRID 1171688 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(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:15][CH2:16][CH:17]\2O)=[N:9][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.[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61]>ClCCl>[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61].[C:38]([S:40][CH:17]1[CH2:16][CH2:15][NH:14][CH2:13]/[C:12]/1=[CH:11]\[C:10]1[N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[N:7]=[N:8][N:9]=1)(=[O:41])[CH3:39]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138766HCID 23138766, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 87565843HCID 87565843, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following a procedure similar to that described in Example 150-(e), (E)-3-{[1-(methoxycarbonylmethyl)-1H-tetrazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (1.5 g) was subjected to the reaction with thioacetic acid and N,N-dimethylformamide dineopentyl acetal. The product was purified by silica gel chromatography to afford (E)-4-(acetylsulfanyl)-3-{([1-(methoxycarbonylmethyl)-1H-tetrazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (980 mg). This product was similarly treated with trifluoroacetic acid in dichloromethane, and the resulting product was purified by silica gel chromatography using dichloromethane and methanol (20:1) as an eluent to afford the title compound (342 mg, overall yield: 27%) as a yellow amorphous solid.

Workup

  1. customThe product was purified by silica gel chromatography
  2. customto afford (E)-4-(acetylsulfanyl)-3-{([1-(methoxycarbonylmethyl)-1H-tetrazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (980 mg)
  3. customthe resulting product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6895a53587944098a1c6507524788158
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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