1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride → (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)-1,3,4-oxadiazol-2-yl)phenyl)propanoate

HRID 1775809Notes

Reaction equation

HRID 1775809 reaction equation
[C:1]([C:5]1[CH:45]=[CH:44][C:8]([C:9]([NH:11][C@@H:12]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([NH:26][NH:27][C:28](=O)[C:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:31][CH:30]=3)=[O:25])=[CH:20][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[CH:45]=[CH:44][C:8]([C:9]([NH:11][C@@H:12]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[O:25][C:28]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:31][CH:30]=4)=[N:27][N:26]=3)=[CH:22][CH:23]=2)[C:13]([O:15][CH3:16])=[O:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 86689659(S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(2-(4-(heptyloxy)benzoyl)hydrazinecarbonyl)phenyl)propanoate

Product 1

HCID 86689658(S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)-1,3,4-oxadiazol-2-yl)phenyl)propanoateYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirring solution (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(2-(4-(heptyloxy)benzoyl)hydrazinecarbonyl)phenyl)propanoate INT-3 (127 mg, 0.21 mmol) and TEA (0.09 mL, 0.62 mmol) in DCM (4 mL) was added 2-chloro-1,3-dimethylimidazolidinium chloride (41.8 mg, 0.25 mmol). The reaction mixture was stirred at room temperature for 18 h then warmed to 40° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with NaHCO3 (15 mL), shaken, split through a hydrophobic frit and evaporated to afford 120 mg (95%) of (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)-1,3,4-oxadiazol-2-yl)phenyl)propanoate as a white solid. LCMS-ESI (m/z) calculated for C36H43N3O5: 597.8. found 598.0 [M+H]+, tR=3.25 min. (Method 4).

Workup

  1. temperaturethen warmed to 40° C. for 1 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringshaken
  4. customsplit through a hydrophobic frit
  5. customevaporated

Sources & evidence

ORD record
ord-3add4f6fbb394974b985cc9d349d777f
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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