Hydrochloric Acid → HCID 67077060, compound

HRID 1055483Notes

Reaction equation

HRID 1055483 reaction equation
[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[H-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[C:19]=1F.Cl>CN(C=O)C.O>[C:11]([O:10][C:8]([NH:1][C@@H:2]([CH2:3][O:4][C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][CH:22]=[CH:23][C:18]=1[F:17])[C:5]([OH:7])=[O:6])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 813351,2-Difluoro-3-nitrobenzeneHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 67077060HCID 67077060, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of BOC-Ser-OH (2.58 g, 12.6 mmol) in DMF (10.00 mL) was added to a suspension of NaH (60% in mineral oil, 1.06 g, 26.4 mmol) in DMF (10 mL) at 0° C. over 10 min. After 1 h at 0° C. a solution of 1,2-difluoro-3-nitrobenzene (2 g, 12.6 mmol) in DMF (10 mL) was added and the mixture stirred at 0° C. for 2 h. The mixture was diluted with H2O and acidified to pH 3 with 1 N HCl, then extracted with EtOAc. The combined extracts were dried over MgSO4 and the filtrate was concentrated to give a residue that was purified by silica gel chromatography to afford (S)-2-(tert-butoxycarbonylamino)-3-(2-fluoro-6-nitrophenoxy)propanoic acid (2.94 g, 68%) as a yellow foam.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts were dried over MgSO4
  3. concentrationthe filtrate was concentrated
  4. customto give a residue that
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-5be269773f4b42c8bd42b12ed16f0155
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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