Water → HCID 86610807, compound

HRID 2112553Notes

Reaction equation

HRID 2112553 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH:16][C:17]([NH:19]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[S:18])([F:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH:16][C:17]([NH2:19])=[S:18])([F:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 86610806HCID 86610806, compound

Product 1

HCID 86610807HCID 86610807, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 4-[({[(fluoren-9-ylmethoxy)carbonylamino]thioxomethyl}amino)methyl]-4-fluoropiperidinecarboxylic acid tert-butyl ester (1896 mg, 3.69 mmol) in DMF (15 ml), piperidine (1.8 ml, 18.5 mmol) was added and the mixture was stirred at room temperature overnight. After completion of the reaction, water (100 ml) was added and extraction was performed with ethyl acetate (100 ml×3 times). The extracted organic layer was washed with water (300 ml×2 times) and then with saturated brine; dried over anhydrous sodium sulfate, and then filtered and concentrated. It was subsequently purified by silica gel column chromatography (hexane/ethyl acetate=1/1, ethyl acetate) to obtain 4-{[(aminothioxomethyl)amino]methyl}-4-fluoropiperidinecarboxylic acid tert-butyl ester. The compound was identified by LC-MS. Yield: 900 mg (84%), M+1=292.1

Workup

  1. additionwas added
  2. additionwas added
  3. extractionextraction
  4. washThe extracted organic layer was washed with water (300 ml×2 times)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customIt was subsequently purified by silica gel column chromatography (hexane/ethyl acetate=1/1, ethyl acetate)

Sources & evidence

ORD record
ord-11c4ea3c0bf64c15b11b9c43d0d0df38
Source dataset
uspto-grants-2009_04
Patent number
US07524841B2

Reaction notes

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