Beta-Alanine → HCID 14580685, compound

HRID 622726Notes

Reaction equation

HRID 622726 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].O1CCCC1.[C:17]([O:20][C@H:21]1[CH2:45][CH2:44][C@@:43]2([CH3:46])[C:23](=[CH:24][CH2:25][C@@H:26]3[C@@H:42]2[CH2:41][CH2:40][C@@:39]2([CH3:47])[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C@H:31]([CH3:38])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:22]1)(Cl)=[O:18]>O.C(Cl)(Cl)Cl>[CH3:37][CH:35]([CH2:34][CH2:33][CH2:32][C@H:31]([C@@H:30]1[C@:39]2([CH3:47])[C@H:27]([C@H:26]3[C@H:42]([CH2:41][CH2:40]2)[C@:43]2([CH3:46])[C:23]([CH2:22][C@@H:21]([O:20][C:17]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:18])[CH2:45][CH2:44]2)=[CH:24][CH2:25]3)[CH2:28][CH2:29]1)[CH3:38])[CH3:36]

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 8028TetrahydrofuranHCID 111262Cholest-5-en-3-ol (3beta)-, 3-(carbonochloridate)HCID 516892Sodium Bicarbonate

Product 1

HCID 14580685HCID 14580685, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of β-alanine (56 mg) and sodium bicarbonate (84 mg) in water (10 ml) were added tetrahydrofuran (20 ml) and cholesterol chlorocarbonate (449 mg) at 0° C. The mixture was stirred for 1 hour. The reaction mixture was concentrated in vacuo and to the residue were added 0.1N hydrochloric acid (10 ml) and chloroform (40 ml). Organic layer was separated, washed with water and dried over magnesium sulfate. Evaporation of the solvent gave a crude product, which was dissolved in chloroform and applied to a silica gel column (40 g). Elution with a mixture of chloroform and methanol gave N-(cholest-5-en-3β-oxycarbonyl)-β-alanine (187 mg) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and to the residue
  2. additionwere added 0.1N hydrochloric acid (10 ml) and chloroform (40 ml)
  3. customOrganic layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a crude product, which
  8. washElution
  9. additionwith a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-e0af3cfa5f8e4aa1bafc0db3e01e9826
Source dataset
uspto-grants-1988_09
Patent number
US04772594

Reaction notes

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