Pyridine → HCID 67995664, compound

HRID 1615123Notes

Reaction equation

HRID 1615123 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([NH:15][CH2:16][CH2:17][C:18]2([OH:28])[CH2:27][CH2:26][CH2:25][C:20]3([O:24][CH2:23][CH2:22][O:21]3)[CH2:19]2)[CH3:14])=[CH:9][CH:8]=1.C(N(CC)CC)C.N1C=CC=CC=1>ClCCl.O>[CH3:5][O:4][C:2](=[O:3])[N:15]([C@H:13]([C:10]1[CH:9]=[CH:8][C:7]([Br:6])=[CH:12][CH:11]=1)[CH3:14])[CH2:16][CH2:17][C:18]1([OH:28])[CH2:27][CH2:26][CH2:25][C:20]2([O:21][CH2:22][CH2:23][O:24]2)[CH2:19]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67995969HCID 67995969, compound

Product 1

HCID 67995664HCID 67995664, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (0.20 mL) is added dropwise to a solution of 7-{2-[(S)-1-(4-bromo-phenyl)-ethylamino]-ethyl}-1,4-dioxa-spiro[4.5]decan-7-ol (0.50 g), triethylamine (0.4 mL), and pyridine (0.2 mL) in dichloromethane (10 mL) chilled in an ice bath. The solution is warmed to room temperature and stirred at this temperature overnight. Water is then added and the resulting mixture is extracted with dichloromethane. The combined extracts are washed with water (3×), dried (MgSO4), and concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. Yield: 0.30 g (50% of theory); Mass spectrum (ESI+): m/z=442/444 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. extractionthe resulting mixture is extracted with dichloromethane
  3. washThe combined extracts are washed with water (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is purified by HPLC on reversed phase (methanol/water)

Sources & evidence

ORD record
ord-60a7602edb0d410ab64fd6ed31e655af
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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