Methanesulfonic Acid → HCID 10530187, compound

HRID 2107648Notes

Reaction equation

HRID 2107648 reaction equation
[C:1]([C:5]1[CH:6]=[C:7](/[CH:22]=[CH:23]/[CH:24]=[CH:25]/[C:26]([NH:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH:34]([C:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[NH:39][CH:38]=3)[CH2:33][CH2:32]2)=[O:27])[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[O:11]COCCOC)([CH3:4])([CH3:3])[CH3:2].CS(O)(=O)=O.[OH-].[Na+].C(=O)(O)[O-].[Na+]>CO>[C:18]([C:9]1[CH:8]=[C:7](/[CH:22]=[CH:23]/[CH:24]=[CH:25]/[C:26]([NH:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH:34]([C:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[NH:39][CH:38]=3)[CH2:33][CH2:32]2)=[O:27])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:19])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23046195HCID 23046195, compound

Product 1

HCID 10530187HCID 10530187, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[2-[5-[3,5-di-tert-butyl-4-{(2-methoxyethoxy)methoxy}phenyl]-(2E,4E)-2,4-pentadienoylamino]ethyl]-4-(3-indolyl)piperidine (0.5 g) in methanol (5 ml) was added dropwise methanesulfonic acid (0.26 ml) at 18°-25° C. After 2 hours the reaction mixture was adjusted to pH 7.5 with 2N-sodium hydroxide and then poured into saturated sodium bicarbonate solution (50 ml). The resulting precipitate was collected and washed with water. The precipitate was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (20:1, V/V). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from 1,4-dioxane, to give white crystals of 1-[2-{5-(3,5-di-tert-butyl-4-hydroxyphenyl)-(2E,4E)-2,4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (0.28 g).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. washeluted with a mixture of chloroform and methanol (20:1, V/V)
  4. additionThe fractions containing the object compound
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-9b45e44039284f9086285835e29a2af3
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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