Hydrochloric Acid → HCID 59166408, compound

HRID 923392Notes

Reaction equation

HRID 923392 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH:7]=[CH2:8])[C:3]([OH:5])=[O:4].C([O-])(O)=O.[Na+].Cl[C:15]([O:17][CH3:18])=[O:16].Cl>O.CCOCC>[CH3:18][O:17][C:15]([NH:1][C@@H:2]([CH2:6][CH:7]=[CH2:8])[C:3]([OH:5])=[O:4])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 167529s-AllylglycineHCID 516892Sodium Bicarbonate

Product 1

HCID 59166408HCID 59166408, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (S)-2-aminopent-4-enoic acid (1.0 g, 8.69 mmol) and NaHCO3 (2.26 mg, 26.9 mmol) in H2O (40 mL) was cooled to 0° C. A mixture of methyl chloroformate (740 μL, 9.55 mmol) dissolved in Et2O (4 mL) was slowly added to the aqueous mixture and stirred for 20 hours coming to ambient temperature. Mixture was adjusted to pH 3.0 with HCl (conc). The mixture was extracted with EtOAc and then dried (MgSO4), filtered and concentrated to afford 1.25 g (83%) of the title compound. MS (ESI) m/z 174 (M+H)+.

Workup

  1. additionwas slowly added to the aqueous mixture
  2. customcoming to ambient temperature
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5fe9626aa91d46f28c9178e06844efaf
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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