Methyl chloroformate → 3-Acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid-methyl ester

HRID 133541Notes

Reaction equation

HRID 133541 reaction equation
[CH3:1][C:2]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1.Cl[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:28][O:27][C:25]([N:8]1[CH2:7][C:6]2[S:5][C:4]3[N:3]=[C:2]([CH3:1])[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[C:11]=2[CH2:10][CH2:9]1)=[O:26]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 688965541-(2-Methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone

Product 1

HCID 115670903-Acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid-methyl esterYield 394.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 50 mg (0.15 mmol) 1-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone (the preparation of which is described in example 23) in 5 ml dichloromethane was added 0.02 ml (0.022 mmol) methyl chloroformate and 32 mg (0.022 mmol) potassium carbonate. The mixture was stirred at RT for 1 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 33 mg (56%) 3-Acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid-methyl ester as a light yellow solid. ES-MS m/e (%): 381 (M+H+, 100);

Workup

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7927c90bcfa4bd096c0d9c99206df9d
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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