2-Mercaptoethanol → HCID 59756976, compound

HRID 2084937Notes

Reaction equation

HRID 2084937 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5](=[C:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)[NH:6][CH:7]=[O:8])[CH3:2].[SH:23][CH2:24][CH2:25][OH:26].C[O-].[Na+]>>[CH2:15]([N:12]1[CH2:13][CH2:14][C:9]([CH:5]([NH:6][CH:7]=[O:8])[C:4]([O:3][CH2:1][CH3:2])=[O:22])([S:23][CH2:24][CH2:25][OH:26])[CH2:10][CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 15672-MercaptoethanolHCID 10942334Sodium MethoxideHCID 86587130HCID 86587130, compound

Product 1

HCID 59756976HCID 59756976, compound

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl(1-benzyl-4-piperidinylidene)(formylamino)acetate (3.0 g, 10.0 mmol), 2-mercaptoethanol (2.7 g, 35 mmol) and sodium methoxide (1 g) was heated at 80° C. for 8 h under nitrogen. The reaction mixture was then cooled to room temperature and quenched with saturated ammonium chloride solution. It was extracted with chloroform, washed twice with brine and dried over anhydrous Na2SO4, filtered and concentrated. The oily residue was purified by silica gel column chromatography eluting with 5% methanol:chloroform to provide ethyl {1-benzyl-4-[(2-hydroxyethyl)sulfanyl]-4-piperidinyl}(formylamino)acetate as a yellow oil; Yield: 2.8 g (73%); Electrospray Mass Spec: 381 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customquenched with saturated ammonium chloride solution
  3. extractionIt was extracted with chloroform
  4. washwashed twice with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oily residue was purified by silica gel column chromatography
  9. washeluting with 5% methanol

Sources & evidence

ORD record
ord-9e623f917763482192f82921db10871c
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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