Hydrochloric Acid → HCID 18770470, compound

HRID 479429Notes

Reaction equation

HRID 479429 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:15]#[C:16]/[CH:17]=[CH:18]/[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([CH2:27][CH:28]([C:54]([O:56]C)=[O:55])[CH2:29][CH:30]3[CH2:35][CH2:34][N:33]([C:36](=[O:53])/[CH:37]=[CH:38]/[C:39]#[C:40][C:41]4[CH:46]=[C:45]([O:47][CH3:48])[C:44]([O:49][CH3:50])=[C:43]([O:51][CH3:52])[CH:42]=4)[CH2:32][CH2:31]3)[CH2:23][CH2:22]2)=[O:20])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12].Cl>CO>[CH3:52][O:51][C:43]1[CH:42]=[C:41]([C:40]#[C:39]/[CH:38]=[CH:37]/[C:36]([N:33]2[CH2:32][CH2:31][CH:30]([CH2:29][CH:28]([C:54]([OH:56])=[O:55])[CH2:27][CH:24]3[CH2:25][CH2:26][N:21]([C:19](=[O:20])/[CH:18]=[CH:17]/[C:16]#[C:15][C:7]4[CH:6]=[C:5]([O:4][CH3:3])[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=4)[CH2:22][CH2:23]3)[CH2:35][CH2:34]2)=[O:53])[CH:46]=[C:45]([O:47][CH3:48])[C:44]=1[O:49][CH3:50]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18770395HCID 18770395, compound

Product 1

HCID 18770470HCID 18770470, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5N aqueous sodium hydroxide (2 ml; 10 mmol) was added to a solution in methanol (2 ml) of methyl 1,3-bis(1-[(E)-5-(3,4,5-trimethoxyphenyl)-2-penten-4-ynoyl]-4-piperidinyl]-2-propanecarboxylate (136 mg; 0.18 mmol) synthesized by the above process, and the mixture was stirred for 1 hour in a bath controlled at 65° C. The reaction mixture was made acidic by addition of 1N hydrochloric acid and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 46 mg (yield: 35%) of the title compound as a pale yellow amorphous powder.

Workup

  1. customsynthesized by the above process
  2. customcontrolled at 65° C
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9524b4a2f658435792a1fb0fc8f808a5
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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