Hexachloroethane → 4-[1-Phenyl-1-(5-(N-(9-fluorenylmethoxycarbonyl)azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester

HRID 606762Notes

Reaction equation

HRID 606762 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:15]([NH:17][NH:18][C:19]([CH:21]2[CH2:24][N:23]([C:25]([O:27][CH2:28][CH:29]3[C:41]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:35]4[C:30]3=[CH:31][CH:32]=[CH:33][CH:34]=4)=[O:26])[CH2:22]2)=[O:20])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:15]2[O:20][C:19]([CH:21]3[CH2:22][N:23]([C:25]([O:27][CH2:28][CH:29]4[C:41]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[C:35]5[C:30]4=[CH:31][CH:32]=[CH:33][CH:34]=5)=[O:26])[CH2:24]3)=[N:18][N:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 670464624-[1-Phenyl-1-(2-(N-(9-fluorenylmethoxycarbonyl)-3-azetidinecarbonyl)-hydrazinocarbonyl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 670463744-[1-Phenyl-1-(5-(N-(9-fluorenylmethoxycarbonyl)azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-[1-phenyl-1-(2-(N-(9-fluorenylmethoxycarbonyl)-3-azetidinecarbonyl)-hydrazinocarbonyl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester (0.411 g, 0.645 mmol), iPr2NEt (0.775 mL, 4.448 mmol) and PPh3 (0.693 g, 2.643 mmol) in CH3CN (8 mL) was added hexachloroethane (0.351 mg, 1.483 mmol). The mixture was allowed to stir for 1 h and then it was worked up as in Method A above and the crude product purified by flash chromatography (SiO2/EtOAc-hexane, 1:1) to give the title compound (0.299 g, 75%) as a colorless solid:

Workup

  1. customthe crude product purified by flash chromatography (SiO2/EtOAc-hexane, 1:1)

Sources & evidence

ORD record
ord-c3b1da05eaa74ca286516ffb967124ad
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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