3,5-Diaminobenzoic acid → 3,5-Bis({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid

HRID 1265943Notes

Reaction equation

HRID 1265943 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH2:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:12](Cl)([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13].[C:30](=[O:33])(O)[O-:31].[Na+]>O>[C:12]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH:11][C:30]([O:31][CH2:15][CH:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3[C:28]2=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:33])[CH:10]=1)[C:5]([OH:7])=[O:6])([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13]

Participants

5

Reactant 3

HCID 120623,5-Diaminobenzoic acidHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 185473023,5-Bis({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound was synthesised from 3,5-diaminobenzoic acid and Fmoc-chloride using sodium bicarbonate as base in a mixture of water and a suitable organic solvent. NMR analytical data were in accordance with the structure.

Sources & evidence

ORD record
ord-da5378e9e493428dbeb38bb398fcd220
Source dataset
uspto-grants-2003_04
Patent number
US06548048B1

Reaction notes

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