Piperidine → HCID 67001364, compound

HRID 561971Notes

Reaction equation

HRID 561971 reaction equation
[C:1]([O:5][C:6](=[O:51])[CH2:7][C@@H:8]([NH:33]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:9]([NH:11][C@H:12]([C:21]1[NH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][CH:27]=2)=[CH:24][N:25]=1)[C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])=[O:10])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:51])[CH2:7][C@@H:8]([NH2:33])[C:9]([NH:11][C@H:12]([C:21]1[NH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][CH:27]=2)=[CH:24][N:25]=1)[C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 67001703HCID 67001703, compound

Product 1

HCID 67001364HCID 67001364, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-succinamic acid tert-butyl ester (1.5 g, 1.88 mmol) (from step 8-G) in methylene chloride (30 mL) was added piperidine (6 mL). The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was purified by chromatography over silica gel gradient eluted from 100% methylene chloride to 10% v/v methanol/methylene chloride in 30 minutes to give ((R)-3-amino-N-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-succinamic acid tert-butyl ester (0.93 g, 86%). LC-MS: calcd for C26H31IN4O3 [M+H+] 575. Found 575.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by chromatography over silica gel gradient
  3. washeluted from 100% methylene chloride to 10% v/v methanol/methylene chloride in 30 minutes

Sources & evidence

ORD record
ord-51b221e3bc19400d82f085bac82da1ba
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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