4-Amino-3-hydroxybutanoic acid → Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate

HRID 1628447Notes

Reaction equation

HRID 1628447 reaction equation
[NH2:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:13](N(CC)CC)C.Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>CO.C(OCC)(=O)C.O1CCCC1>[N+:30]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([N+:27]([O-:29])=[O:28])[C:21]=1[NH:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([O:7][CH3:13])=[O:6])([O-:32])=[O:31]

Participants

8

Reactant 4

HCID 21494-Amino-3-hydroxybutanoic acidHCID 8471TriethylamineHCID 118141-Chloro-2,6-dinitrobenzeneHCID 24386Thionyl Chloride

Product 1

HCID 86632868Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoateYield 100.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of rac-4-amino-3-hydroxybutyric acid (2.00 g, 16.8 mmol) in methanol (40 mL) was added thionyl chloride (1.72 mL, 23.6 mmol) at 0° C. The resultant mixture was stirred at room temperature for 1 hr and concentrated in vacuo. To a mixture of the residue, triethylamine (5.85 mL, 42.0 mmol) and tetrahydrofuran (34 mL) was added 2-chloro-1,3-dinitrobenzene (1.70 g, 8.39 mmol) at room temperature. After the resultant mixture was stirred at 50° C. for 2 hr, the mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (2.53 g, 8.45 mmol, quant).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3145a0841014183a88aeb0ffa2b3408
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…