Water → (R)-2-(benzyloxycarbonylamino)-3-methyl-3-(2-nitrophenylthio)butanoic acid

HRID 1055415Notes

Reaction equation

HRID 1055415 reaction equation
C([O-])(O)=O.[Na+].O.[CH2:7]([O:14][C:15]([NH:17][C@@H:18]([C:22]([SH:25])([CH3:24])[CH3:23])[C:19]([OH:21])=[O:20])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34]>CCO>[CH2:7]([O:14][C:15]([NH:17][C@@H:18]([C:22]([CH3:23])([S:25][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34])[CH3:24])[C:19]([OH:21])=[O:20])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 738951-Fluoro-2-nitrobenzeneHCID 516892Sodium BicarbonateHCID 22881903(R)-2-(((Benzyloxy)carbonyl)amino)-3-mercapto-3-methylbutanoic acid

Product 1

HCID 90037688(R)-2-(benzyloxycarbonylamino)-3-methyl-3-(2-nitrophenylthio)butanoic acidYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaHCO3 (14.5 g, 172 mmol, Eq: 2.5) and H2O (210 mL) were added to a slurry of (R)-2-(benzyloxycarbonylamino)-3-mercapto-3-methylbutanoic acid (19.5 g, 68.8 mmol, Eq: 1.00) in EtOH (70.0 mL). After 20 min. the mixture became homogeneous, 1-fluoro-2-nitrobenzene (9.71 g, 7.00 mL, 68.8 mmol, Eq: 1.00) was added and the mixture heated to reflux for 6 h. The mixture was cooled to RT, poured into H2O (300 mL) and extracted with MTBE. The aqueous layer was acidified to pH 5 with 1 N HCl and extracted with Et2O. The combined organic extracts were dried over Na2SO4 filtered and concentrated to give (R)-2-(benzyloxycarbonylamino)-3-methyl-3-(2-nitrophenylthio)butanoic acid (18.7 g, 67.2%) as a light yellow oil which was used without purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 6 h
  3. extractionextracted with MTBE
  4. extractionextracted with Et2O
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c31102fa68c5410d979d706cbbb6f075
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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