9-Fluorenylmethyl chloroformate → 5-{[(9h-Fluoren-9-ylmethoxy)carbonyl]amino}-2,4-dimethylbenzenesulfonic acid

HRID 1802460Notes

Reaction equation

HRID 1802460 reaction equation
[Na+].[NH2:2][C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([S:9]([O-:12])(=[O:11])=[O:10])[CH:8]=1.C([O-])(O)=O.[Na+].Cl[C:21]([O:23][CH2:24][CH:25]1[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22]>O1CCOCC1.O>[CH:36]1[C:37]2[CH:25]([CH2:24][O:23][C:21]([NH:2][C:3]3[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([S:9]([OH:12])(=[O:10])=[O:11])[CH:8]=3)=[O:22])[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]=2[CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 23691697Sodium 5-amino-2,4-dimethylbenzene-1-sulfonate

Product 1

HCID 594360375-{[(9h-Fluoren-9-ylmethoxy)carbonyl]amino}-2,4-dimethylbenzenesulfonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-amino-2,4-dimethylbenzenesulfonic acid sodium salt (3.0 g, 13.4 mmol) in dioxane (37 mL) and water (37 ml) was added NaHCO3 (2.5 g, 29.6 mmol) and 9-fluoreneylmethyl chloroformate. The mixture was then stirred at room temperature overnight and then quenched with 1N HCl and extracted with EtOAc. The organic layers were concentrated in vacuo. Purification by silica gel chromatography (0-10% MeOH/DCM) resulted in the title compound.

Workup

  1. customquenched with 1N HCl
  2. extractionextracted with EtOAc
  3. concentrationThe organic layers were concentrated in vacuo
  4. customPurification by silica gel chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-bbd3401ec28f4774b4dbb717bfe4205d
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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