Hydrochloric Acid → (S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acid

HRID 1055356Notes

Reaction equation

HRID 1055356 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][OH:16])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].Cl>CN(C=O)C>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][O:16][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 18599736(S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% in mineral oil, 2.88 g, 72 mmol) in DMF (25 mL) at 0° C. was added (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (7 g, 34 mmol) in DMF (25 mL). After 2 h 1-fluoro-2-nitrobenzene (5.29 g, 37.5 mmol) in DMF (25 mL) was added and the resulting mixture stirred for 3 h at 0° C. The mixture was poured into ice/H2O (200 mL), acidified to pH 5.0 with 1 N HCl and extracted with EtOAc. The combined extracts were dried over Na2SO4, concentrated and purified by flash chromatography to give (S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenoxy)-propionic acid (10.9 g, 97%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-18cdf85b907b49998899e11338d25799
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…