Sodium Iodide → HCID 117856653, compound

HRID 509896Notes

Reaction equation

HRID 509896 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.[C:30](=[O:33])([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(O)(=O)C>[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][N:10]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:33][CH3:30])=[CH:24][CH:23]=1)[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 127769961-(3-Bromopropyl)-4-methoxybenzeneHCID 16740609tert-butyl N-(2-amino-1-phenylethyl)carbamate

Product 1

HCID 117856653HCID 117856653, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-amino-1-phenyl-ethyl-carbamic acid tert-butylester (47 mg, 0.2 mmol), 1-(3-Bromo-propyl)-4-methoxy-benzene (100 mg, 0.44 mmol), potassium carbonate (82 mg, 0.6 mmol) and sodium iodide (5 mg, 0.03 mmol) in acetonitrile is stirred at 80° C. for one night. The reaction mixture is acidified with acetic acid, concentrated under reduced pressure and the product is purified by preparative HPLC-MS (50° C., gradient: 45-65% MeOH/H2O+0.1% TFA). The solvent is removed under reduced pressure. Mass spectrum (ESI+): m/z=533 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe product is purified by preparative HPLC-MS (50° C., gradient: 45-65% MeOH/H2O+0.1% TFA)
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e3b34e1f50dd4f19afcb0a037b3681c5
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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