9-Fluorenylmethyl chloroformate → HCID 54202138, compound

HRID 1263561Notes

Reaction equation

HRID 1263561 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3].[NH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][CH:25]=1>C1COCC1.C([O-])(O)=O.[Na+].CCOC(C)=O.O>[CH:17]1[C:18]2[CH:6]([CH2:5][O:4][C:2]([CH:20]([NH2:19])[CH2:21][CH2:22][CH2:23][C:24]3[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[CH:26][CH:25]=3)=[O:3])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 18617216HCID 18617216, compound

Product 1

HCID 54202138HCID 54202138, compoundYield 68.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

9-Fluorenylmethyl chloroformate (6.9 g) was added to biphasic mixture of tert-butyl 4-(4-aminobutyl)benzoate (5.7 g) in THF (100 mL) and saturated aqueous NaHCO3 (50 mL). The resulting mixture was stirred at r.t. for 1 h and then diluted with EtOAc and H2O. The organic layer was separated and washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography to give 7.4 g of tert-butyl 4-(4-(9-fluorenylmethoxycarbonyl)-aminobutyl)benzoate.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-89dcc0419cb54b3290dfcfab236a206e
Source dataset
uspto-grants-2003_04
Patent number
US06541492B1

Reaction notes

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