Sodium Hydroxide → HCID 131719249, compound

HRID 375411Notes

Reaction equation

HRID 375411 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 2X with EtOAc. The organic fraction was dried (Na2SO4) and concentrated under reduced pressure. Recrystallization of the residue 3X 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). Anal. calc'd. for C14H21NO5 : C, 59.35; H, 7.47; N, 4.94.

Workup

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

Sources & evidence

ORD record
ord-9cb18b6c9a944c9cb78ff3d0585264e0
Source dataset
uspto-grants-1996_01
Patent number
US05484946

Reaction notes

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