Piperidine → HCID 89835598, compound

HRID 2277101Notes

Reaction equation

HRID 2277101 reaction equation
N1CCCCC1.C1C2C(COC([N:24]3[CH2:29][CH2:28][S:27][CH2:26][C@H:25]3[C:30](=[O:49])[NH:31][CH2:32][C:33]3[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=3[CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=O)C3C(=CC=CC=3)C=2C=CC=1>C(Cl)Cl>[C:45]([O:44][C:42](=[O:43])[NH:41][CH2:40][C:34]1[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:33]=1[CH2:32][NH:31][C:30]([C@@H:25]1[CH2:26][S:27][CH2:28][CH2:29][NH:24]1)=[O:49])([CH3:48])([CH3:46])[CH3:47]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 89824877HCID 89824877, compound

Product 1

HCID 89835598HCID 89835598, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperidine (0.95 mL, 9.65 mmol) was added dropwise to a stirred solution of (R)-(9H-Fluoren-9-yl)methyl-3-[2-{(tert-butoxycarbonylamino)methyl}-5-chloro benzylcarbamoyl]thiomorpholine-4-carboxylate (1.20 g, 1.93 mmol) in CH2Cl2 (50 mL) and the resulting mixture was stirred at room temperature for 2 h. Volatile solvent was removed under reduced pressure and the residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile:water) to afford the title compound (0.64 g) as a white solid.

Workup

  1. customVolatile solvent was removed under reduced pressure
  2. customthe residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile:water)

Sources & evidence

ORD record
ord-86351754f9284b1197390282aeb42fec
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

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