Hydrochloric Acid → HCID 12221517, compound

HRID 2101934Notes

Reaction equation

HRID 2101934 reaction equation
O=[C:2]([CH3:11])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].Cl.[OH-].[NH4+:14]>CO>[NH2:14]/[C:2](/[CH3:11])=[CH:3]\[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 15538Tert-butyl acetoacetate

Product 1

HCID 12221517HCID 12221517, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,1-dimethylethyl 3-oxobutanoate (50 g, 0.32 mol) in MeOH (320 mL) and 30% ammonium hydroxide (280 mL) was stirred at ambient temperature overnight. The solution was neutralized carefully with conc. HCl (200 mL), partially concentrated at reduced pressure and extracted with EtOAc (2×300 mL). Combined organic phases were dried over Na2SO4, filtered and concentrated to afford 1,1-dimethylethyl (2Z)-3-amino-2-butenoate as an oil that crystallized on standing (54 g, 100% yield): 1H NMR (DMSO-d6) δ 7.63 (bs, 1H), 6.79 (bs, 1H), 4.18 (s, 1H), 1.74 (s, 3H), 1.35 (s, 9H).

Workup

  1. concentrationpartially concentrated at reduced pressure
  2. extractionextracted with EtOAc (2×300 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5baa485091ef4b318478ac843eaa2ca2
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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