Hydrochloric Acid → HCID 72338057, compound

HRID 71935Notes

Reaction equation

HRID 71935 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][CH:7]([CH2:11][C:12]#[N:13])[C:8]([OH:10])=[O:9].[OH-].[Na+].Cl>C1COCC1>[C:12]([CH2:11][CH:7]([NH:6][C:2]([O:4][CH3:5])=[O:3])[C:8]([OH:10])=[O:9])#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 13538beta-CyanoalanineHCID 14798Sodium Hydroxide

Product 1

HCID 72338057HCID 72338057, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl chloroformate (0.81 mL, 10.51 mmol) was added dropwise to a stirred suspension of 2-Amino-3-cyano-propionic acid (1.00 g, 8.76 mmol) and NaOH (5 N in H2O, 4.2 mL, 21.0 mmol) in THF (20 mL). After stirring at room temperature for 7 h, the reaction mixture was poured into 10% HCl and the aqueous phase was extracted 3× with diethyl ether. The combined organics were dried over MgSO4, filtered and concentrated to afford 3-Cyano-2-methoxycarbonylamino-propionic acid (295 mg, 20%).

Workup

  1. extractionthe aqueous phase was extracted 3× with diethyl ether
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8108dfd370e141a2b4b0c794d3646ac4
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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