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

HRID 1394443Notes

Reaction equation

HRID 1394443 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:15]2[O:16][C:17]([CH:20]3[CH2:23][N:22](C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:21]3)=[N:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(S)CCCCCC>C1COCC1.C1CCN2C(=NCCC2)CC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:15]2[O:16][C:17]([CH:20]3[CH2:21][NH:22][CH2:23]3)=[N:18][N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 154221-HeptanethiolHCID 670463744-[1-Phenyl-1-(5-(N-(9-fluorenylmethoxycarbonyl)azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 670464414-[1-Phenyl-1-(5-(azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl esterYield 74.7%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 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(0.161 g, 0.260 mmol) and heptanethiol (0.398 mL, 2.60 mmol) in THF (2.6 mL) at rt was added DBU (2 drops). The mixture was allowed to stir for 18 h and then the solvent was removed in vacuo. The residue was dissolved in MeOH and purified by preparative HPLC (NH4OAc) to afford the title compound (0.077 g, 74%) as a colorless solid:

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. custompurified by preparative HPLC (NH4OAc)

Sources & evidence

ORD record
ord-2d607c958dfb4d49b25aa88e082ffc3b
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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