Sodium Hydroxide → HCID 131719249, compound

HRID 976095Notes

Reaction equation

HRID 976095 reaction equation
Cl.[NH2:2][CH:3]([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH-:11].[Na+]>CCOC(C)=O>[C:5]([OH:7])(=[O:6])[C@@H:4]([C:3]1[CH:10]=[CH:5][CH:4]=[CH:3][CH:10]=1)[OH:11].[NH2:2][C@H:3]([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 74821439Butanoic acid, 3-aMino-, ethyl ester, hydrochloride

Product 1

HCID 131719249HCID 131719249, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 3-aminobutyrate hydrochloride (4.5 g, 26.8 mmol) in 27 mL of 1N NaOH was extracted 2× with EtOAc. The organic fraction was dried (Na2SO4) and concentrated under reduced pressure. Recrystallization of the residue 3× from EtOAc afforded 1.93 g (51%) of product as a single chiral diastereomer as determined by NMR spectroscopy (m.p. 125°-125° C.). 1H-NMR (300 MHz, CDCl3) δ1.00 (d, J=7 Hz, 3H), 1.27 (t, J=7 Hz, 3H), 2.23-2.45 (m, 2H), 3.13 (m, 1H), 4.13 (q, J=7 Hz, 2H), 4.85 (s, 1H), 7.17-7.33 (m, 3H), 7.41 (d, J=8 Hz, 2H).

Workup

  1. dry with materialThe organic fraction was dried (Na2SO4)
  2. concentrationconcentrated under reduced pressure
  3. customRecrystallization of the residue 3× from EtOAc

Sources & evidence

ORD record
ord-a0e6545474014cb282b3e862efbede46
Source dataset
uspto-grants-1997_03
Patent number
US05610296

Reaction notes

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