Pentafluorophenol → Pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

HRID 1289223Notes

Reaction equation

HRID 1289223 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH:12]2[C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][C:15]=3[CH2:14][CH2:13]2)[N:22]=[C:21]([CH3:25])[N:20]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:19]4=[O:34])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:35][C:36]1[C:41](O)=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:37]=1[F:46].ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH:12]2[C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][C:15]=3[CH2:14][CH2:13]2)[N:22]=[C:21]([CH3:25])[N:20]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:32])[CH3:31])[C:19]4=[O:34])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:41]1[C:40]([F:43])=[C:39]([F:44])[C:38]([F:45])=[C:37]([F:46])[C:36]=1[F:35])=[O:5]

Participants

5

Reactant 3

HCID 13041PentafluorophenolHCID 757711-HydroxybenzotriazoleHCID 19066365o-Fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoic acid

Product 1

HCID 19066345Pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]-benzoic acid (0.75 g), pentafluorophenol (1.77 g), N,N-dicyclohexylcarbodiimide (0.66 g), N-hydroxybenzotriazole (0.01 g) and methylene chloride (100 ml) was stirred at ambient temperature for 18 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate as eluant. There was thus obtained pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate as a gum (0.72 g);

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography
  4. temperatureusing increasingly polar mixtures of hexane and ethyl acetate as eluant

Sources & evidence

ORD record
ord-6be7575db97240039c67d6effab86d2c
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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