DL-Serine → HCID 12942449, compound

HRID 904176Notes

Reaction equation

HRID 904176 reaction equation
[NH2:1][CH:2]([C:5]([OH:7])=O)[CH2:3][OH:4].[OH-].[Na+].[CH2:10]([N:14]=[C:15]=[O:16])[CH2:11][CH2:12][CH3:13]>O>[CH2:10]([N:14]1[C:5](=[O:7])[CH:2]([CH2:3][OH:4])[NH:1][C:15]1=[O:16])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 617DL-SerineHCID 8110Butyl isocyanateHCID 14798Sodium Hydroxide

Product 1

HCID 12942449HCID 12942449, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

DL-Serine (5.0 g) was dissolved in water (25 ml) containing sodium hydroxide (23.8 ml, 2N) and the mixture cooled to 0° C., stirred and n-butyl isocyanate (9.4 g) added. The mixture was stirred at 0° C. for 2 hours then allowed to rise to room temperature overnight, filtered and the filtrate acidified with concentrated hydrochloric acid (50 ml) and heated on a steam-bath for 2 hours. The mixture was cooled and extracted with ether (3×100 ml). Removal of the ether gave an oil which rapidly crystallised and the title product recrystallised from carbon tetrachloride as small cubes, m.p. 93° C. Yield 5.1 g=57%.

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 hours
  2. filtrationfiltered
  3. temperatureheated on a steam-bath for 2 hours
  4. temperatureThe mixture was cooled
  5. extractionextracted with ether (3×100 ml)
  6. customRemoval of the ether
  7. customgave an oil which
  8. customrapidly crystallised
  9. customthe title product recrystallised from carbon tetrachloride as small cubes, m.p. 93° C

Sources & evidence

ORD record
ord-9e13de37aadd4b7b9fa4113108de1086
Source dataset
uspto-grants-1980_10
Patent number
US04230716

Reaction notes

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