Sarcosine → HCID 14129402, compound

HRID 978044Notes

Reaction equation

HRID 978044 reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].[C:7](Cl)(=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>[OH-].[Na+].CCOCC>[C:7]([N:1]([CH3:2])[CH2:3][C:4]([OH:6])=[O:5])(=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Procedure

Sarcosine (1.78 g, 20 mmol) was dissolved in 1N NaOH solution (40 ml) and Et2O (40 ml) was added. After cooling in an ice bath a solution of hexanoyl chloride (3.1 ml, 22 mmol) in Et2O (10 ml) was added dropwise. The mixture was stirred cold for 1 hour. The pH was then adjusted to about 8 by adding 1N NaOH solution (about 3 ml) and the mixture was stirred at room temperaturee 45 minutes. NaOH solution was added to about pH 9-10. The layers were separated and the aqueous layer was washed with Et2O (50 ml). After acidification of the aqueous layer with concentrated HCl and saturation with solid KCl, the product was extracted into CHCl3 (3×70 ml). The combined CHCl3 extracts were washed with saturated NaCl solution (25 ml), dried (MgSO4), and freed of solvent leaving the title compound as an oil (3.78 g, quant.) which was used without further purification.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at room temperaturee 45 minutes
  3. customThe layers were separated
  4. washthe aqueous layer was washed with Et2O (50 ml)
  5. extractionAfter acidification of the aqueous layer with concentrated HCl and saturation with solid KCl, the product was extracted into CHCl3 (3×70 ml)
  6. washThe combined CHCl3 extracts were washed with saturated NaCl solution (25 ml)
  7. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-bd115c90ccfe454a9fae2d3ea3a7cab7
Source dataset
uspto-grants-1987_05
Patent number
US04663336

Reaction notes

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