1-Fluoro-2-nitrobenzene → HCID 54305290, compound

HRID 1741524Notes

Reaction equation

HRID 1741524 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[CH:32](CN)[C:33]([OH:35])=[O:34])=O)(C)(C)C.F[C:39]1C=CC=CC=1[N+]([O-])=O.C(=O)(O)[O-].[Na+]>O.CN(C)C=O>[CH3:39][O:35][C:33](=[O:34])[CH2:32][N:21]1[C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2

Participants

7

Reactant 4

HCID 738951-Fluoro-2-nitrobenzeneHCID 516892Sodium BicarbonateHCID 32971953-Amino-2-{[(tert-butoxy)carbonyl]amino}propanoic acidHCID 22881947N-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanine

Product 1

HCID 54305290HCID 54305290, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2(S)-tert-Butoxycarbonylamino-3-(2-nitrophenyl-amino)-propionic acid. 2-tert-Butoxycarbonylamino-3-aminopropionic acid (10 g, 49 mmol), 2-fluoronitrobenzene (5.7 ml, 54 mmol), and sodium bicarbonate (8.25 g, 98 mmol) was taken into 130 ml of dimethylformamide and heated at 80° C. for 18 hours. The reaction was evaporated in vacuo to give a viscous orange residue that was dissolved in 300 ml of water and extracted with diethyl ether (3×150 ml). The aqueous solution was acidified to pH 5 with 10% sodium hydrogen sulfate and extracted with ethyl acetate (3×250 ml). The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to give 12.64 g (83 %) of the title compound as an orange amorphous solid. 1H NMR (CD3OD) δ8.15-8.10 (1H,d), 7.54-7.48 (1H,t), 7.13-7.08 (1H, d), 6.73-6.65 (1H, t), 4.45-4.35 (1H, m), 3.9-3.8 (1H, dd), 3.65-3.55 (1H, dd), 1.45 (9H, s).

Workup

  1. customThe reaction was evaporated in vacuo
  2. customto give a viscous orange residue that
  3. extractionextracted with diethyl ether (3×150 ml)
  4. extractionextracted with ethyl acetate (3×250 ml)
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-740bf9997bcc476b8f0f243e4a41407d
Source dataset
uspto-grants-1999_10
Patent number
US05973111

Reaction notes

Loading…