9-Fluorenylmethyl carbazate → 5-[N'-(9H-fluoren-9-ylmethoxycarbonyl)hydrazino]-5-oxo-3-phenylpentanoic acid

HRID 480006Notes

Reaction equation

HRID 480006 reaction equation
[C:1]1([CH:7]2[CH2:13][C:12](=[O:14])[O:11][C:9](=[O:10])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([NH:32][NH2:33])([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16]>C1COCC1>[CH:21]1[C:20]2[CH:19]([CH2:18][O:17][C:15]([NH:32][NH:33][C:12](=[O:14])[CH2:13][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][C:9]([OH:11])=[O:10])=[O:16])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 1618839-Fluorenylmethyl carbazateHCID 2978824-Phenyloxane-2,6-dione

Product 1

HCID 106945935-[N'-(9H-fluoren-9-ylmethoxycarbonyl)hydrazino]-5-oxo-3-phenylpentanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 mmol of 3-phenylglutaric anhydride and 2.0 mmol of Fmoc-hydrazine are dissolved in 30 ml of THF and heated under reflux for 16 hours. The product is then extracted with 50 ml of DCM and 50 ml of 1N HCl solution and the organic phase is dried with MgSO4 and filtered off. Removal of the solvent gives 5-[N′-(9H-fluoren-9-ylmethoxycarbonyl)hydrazino]-5-oxo-3-phenylpentanoic acid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. extractionThe product is then extracted with 50 ml of DCM and 50 ml of 1N HCl solution
  4. dry with materialthe organic phase is dried with MgSO4
  5. filtrationfiltered off
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-9cd8bef05875445da19818467726c812
Source dataset
uspto-grants-2003_11
Patent number
US06649613B1

Reaction notes

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