9-Fluorenylmethyl chloroformate → 3-Nitrobenzoic acid

HRID 1434482Notes

Reaction equation

HRID 1434482 reaction equation
NC[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].ClC(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O>C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>[N+:12]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:3]=1)[C:7]([OH:9])=[O:8])([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 120859504-Aminomethyl-3-nitrobenzoic acid

Product 1

HCID 84973-Nitrobenzoic acidYield 92%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

4-(Aminomethyl)-3-nitrobenzoic acid G (0.8 g; 4 mmol) was dissolved in 10% aq. Na2CO3 (25 mL) and 1,4-dioxane (10 mL) and the solution was cooled to 0° C. A solution of 9-fluorenylmethyl chloroformate (Fmoc-Cl) (1.06 g; 4 mmol) in 1,4-dioxane (10 mL) was added dropwise for 20 min. After 2 h at 0-5° C. and 1 h at 10° C. the reaction mixture was filtered and the solution was acidified to pH 5 by addition of 1 N HCl. The precipitate was filtered, washed with H2O (2×2 mL) dried under vacuum (1.3 kPa; P2O5) to give 4-[[[9H-fluoren-9-ylmethoxy)carbonyl]amino]methyl]-3-nitrobenzoic acid as a white solid (1.6 g; 3.7 mmol). Yield 92%.

Workup

  1. filtration1 h at 10° C. the reaction mixture was filtered
  2. additionthe solution was acidified to pH 5 by addition of 1 N HCl
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O (2×2 mL)
  5. dry with materialdried under vacuum (1.3 kPa; P2O5)

Sources & evidence

ORD record
ord-55261f00de3447be966478ab057b0ff8
Source dataset
uspto-grants-2009_11
Patent number
US07611692B2

Reaction notes

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