N-(9-Fluorenylmethoxycarbonyloxy)succinimide → 173911-21-2

HRID 735847Notes

Reaction equation

HRID 735847 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=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:13]=[CH:12][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:2]([OH:4])=[O:3])[CH:6]=2)=[CH:18][CH:17]=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 67186951578026-45-6

Product 1

HCID 67187541173911-21-2Yield 47.5%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-(3-carboxyphenyl)benzylamine hydrochloride (20 g, 0.075 mol) in 10% Na2CO3 (350 mL) and dioxane (100 mL) was cooled to 0° C. with stirring. A solution of Fmoc-OSu (30.7 g, 0.091 mol) in dioxane (100 mL) was added in one portion and the reaction mixture was stirred at RT for 3 h. Acidified with 1.5 N aqueous solution of HCl and extracted with EtOAc (3×400 mL). The organic layer was washed with water (3×500 mL), brine dried over Na2SO4 and concentrated, purification by column chromatography using dichloromethane/methanol (9:1) to give N-Fmoc-4-(3-carboxyphenyl)benzylamine (16 g). This was further purified by recrystallization from THF/PetEther gave the title pure product (8 g).

Workup

  1. stirringthe reaction mixture was stirred at RT for 3 h
  2. extractionAcidified with 1.5 N aqueous solution of HCl and extracted with EtOAc (3×400 mL)
  3. washThe organic layer was washed with water (3×500 mL), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurification by column chromatography

Sources & evidence

ORD record
ord-2cb6e14ead4d4155a3a08b0682297e52
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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