Sodium hydride → (S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid

HRID 1055369Notes

Reaction equation

HRID 1055369 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][OH:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26]>CN(C=O)C.OS([O-])(=O)=O.[K+]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 67076916(S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acidYield 83.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516920Potassium bisulfateSolvent

Procedure

(S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (5.5 g, 26.8 mmol, Eq: 1.00) was dissolved in DMF (90 mL) at 0° C. and NaH (60% in mineral oil, 2.57 g, 64.3 mmol, Eq: 2.4) was added in small portions The mixture was stirred for 30 min. and 2-fluoro-4-methyl-1-nitrobenzene (4.16 g, 26.8 mmol, Eq: 1.00) in DMF (10 mL) was added dropwise. The resulting mixture was stirred for 60 min., diluted with 1.0 M KHSO4 and extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford (S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid (7.60 g, 83%) as red oil.

Workup

  1. stirringThe resulting mixture was stirred for 60 min.
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4d12c16aa3f94ad49face4bf66a2219e
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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