N-(9-Fluorenylmethoxycarbonyloxy)succinimide → HCID 67187482, compound

HRID 735863Notes

Reaction equation

HRID 735863 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([OH:4])=[O:3].[C:19](ON1C(=O)CCC1=O)([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20]>C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>[C:19]([NH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:2]([OH:4])=[O:3])=[CH:10][CH:9]=2)=[CH:12][CH:13]=1)([O:21][CH2:22][CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:20]

Participants

5

Reactant 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 67186939578026-68-3

Product 1

HCID 67187482HCID 67187482, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

4-(4-Carboxyphenyl)benzylamine hydrochloride (10 g, 0.038 mol) was taken in a mixture of 10% Na2CO3 (100 mL) and dioxane (25 mL). To this a solution of Fmoc-OSu (15.4 g, 0.045 mol) in dioxane (50 mL) was added at 10° C. and the reaction was stirred at RT for 4 h. Solvent was removed under reduced pressure and the residue was acidified with an aqueous solution of HCl (1.5 N), extracted with EtOAc and the crude was recrystallised from EtOAc to give N-Fmoc-4-(4-carboxyphenyl)benzylamine (8.5 g, 45%).

Workup

  1. customSolvent was removed under reduced pressure
  2. extractionextracted with EtOAc
  3. customthe crude was recrystallised from EtOAc

Sources & evidence

ORD record
ord-56e56d8bcb36489cb5af9a8c645847d0
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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