Piperidine → HCID 68618482, compound

HRID 1433758Notes

Reaction equation

HRID 1433758 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([C:30](=[O:40])[NH:31][C:32]3[CH:37]=[CH:36][C:35]([I:38])=[CH:34][C:33]=3[F:39])[CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>ClCCl>[NH2:17][C@@H:18]([CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[C:30]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([I:38])=[CH:34][C:33]=1[F:39])=[O:40]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68620063HCID 68620063, compound

Product 1

HCID 68618482HCID 68618482, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(2-fluoro-4-iodo-phenylcarbamoyl)-2-naphthalen-2-yl-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (1.05 g, 1.60 mmol) in dichloromethane (24 mL) was added piperidine (6 mL) and the mixture stirred at room temperature for 1 hour. After removal of the solvent, the residue was purified by chromatography over silica gel gradient eluted from 100% hexane up to 40% ethyl acetate/60% hexane in 30 minutes. Concentration of the product containing fractions gave (S)-2-amino-N-(2-fluoro-4-iodo-phenyl)-3-naphthalen-2-yl-propionamide as a yellow solid (390 mg, 56%).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by chromatography over silica gel gradient
  3. washeluted from 100% hexane up to 40% ethyl acetate/60% hexane in 30 minutes
  4. additionConcentration of the product containing fractions

Sources & evidence

ORD record
ord-a1130d68181c40058c27e7c0e10359a9
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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