Beta-Alanine → HCID 14557735, compound

HRID 2371971Notes

Reaction equation

HRID 2371971 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[CH2:13]([O:15][C:16]([C@@H:18]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:19][C@H:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21](Cl)=[O:22])=[O:17])[CH3:14]>O>[CH2:13]([O:15][C:16]([C@@H:18]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:19][C@H:20]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:21]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:22])=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 10340Sodium CarbonateHCID 53863562HCID 53863562, compound

Product 1

HCID 14557735HCID 14557735, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of 1.5 g of 3-aminopropionic acid and 1.8 g of sodium carbonate in 30 ml of water at 0° is added to 2.2 g of 4-ethoxycarbonyl-(R*,R*)-2,4-dibenzylbutyryl chloride and the mixture is stirred at room temperature for 4 hours. The mixture is extracted with ether, and the aqueous layer is acidified with 2N hydrochloric acid. The acidic solution is extracted with ethyl acetate, washed with saturated brine, dried (magnesium sulfate), filtered and concentrated. The residue is recrystallized from ether to yield N-[4-ethoxycarbonyl-(R*,R*)-2,4-dibenzylbutyryl]-3-aminopropionic acid, melting at 84°-86°; NMR (CDCl3) δ10.5 (1H, CO2H), 6.1 (t, 1H, J=6 Hz, NH), 4.1 (q, 2H, J=8 Hz, OCH2), 1.08 (t, 3H, J=8 Hz, CH3).

Workup

  1. extractionThe mixture is extracted with ether
  2. extractionThe acidic solution is extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is recrystallized from ether

Sources & evidence

ORD record
ord-8d5d789a215443ca83e48668db3181e1
Source dataset
uspto-grants-1992_03
Patent number
US05096925

Reaction notes

Loading…