Fmoc isothiocyanate → HCID 86610806, compound

HRID 2112552Notes

Reaction equation

HRID 2112552 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH2:16])([F:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1[C:29]2[CH:28]([CH2:30][O:31][C:32]([N:34]=[C:35]=[S:36])=[O:33])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:15][NH:16][C:35]([NH:34][C:32]([O:31][CH2:30][CH:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:21]3[C:29]2=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:33])=[S:36])([F:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4154759Fmoc isothiocyanateHCID 40152119tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate

Product 1

HCID 86610806HCID 86610806, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 4-(aminomethyl)-4-fluoropiperidinecarboxylic acid tert-butyl ester (1071 mg, 4.61 mmol) in tetrahydrofuran (10 ml), FmocNCS (9-fluorenylmethoxycarbonyl isothiocyanate) (1425 mg, 5.07 mmol) was added and the mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was concentrated and purified by silica gel column chromatography (hexane/ethyl acetate=10/1-5/1) to obtain 4-[({[(fluoren-9-ylmethoxy)carbonylamino] thioxomethyl}amino)methyl]-4-fluoropiperidinecarboxylic acid tert-butyl ester. The compound was identified by LC-MS.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated
  4. custompurified by silica gel column chromatography (hexane/ethyl acetate=10/1-5/1)

Sources & evidence

ORD record
ord-8b1d33fd8f8749bd8b2d1c2b6fb6b881
Source dataset
uspto-grants-2009_04
Patent number
US07524841B2

Reaction notes

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