Hydrochloric Acid → N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-hydroxy-2-(3-formamido-4-benzyloxyphenyl) ethylamine monohydrochloride

HRID 226291Notes

Reaction equation

HRID 226291 reaction equation
[OH:1][C@H:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@H:15]([OH:33])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:18]([NH:30][CH:31]=[O:32])[CH:17]=2)=[CH:7][CH:6]=1.[ClH:40].O1CCOCC1>CC(O)C>[ClH:40].[OH:1][C@H:2]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@H:15]([OH:33])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:18]([NH:30][CH:31]=[O:32])[CH:17]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57755061N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-hydroxy-2-(3-formamido-4-benzyloxyphenyl) ethylamine

Product 1

HCID 86613492N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-hydroxy-2-(3-formamido-4-benzyloxyphenyl) ethylamine monohydrochlorideYield 69%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Seed crystals were obtained as follows. N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-hydroxy-2-(3-formamido-4-benzyloxyphenyl)ethylamine (96.1 mg, 0.18 mmol) was dissolved in 2-propanol (2.2 mL) with warming. A solution of hydrochloric acid in dioxane (4 M, 45 μL, 0.18 mmol) was added. At the end of the addition the majority of material was present as a gum which was stirred at room temperature overnight. The solids were collected by filtration, washed with 2-propanol (3×1 mL) and dried by suction on the filter to give the title compound as a colorless solid (69.5 mg, 69%). 1H NMR in accord with structure (400 MHz, DMSO-d6).

Workup

  1. customSeed crystals were obtained
  2. temperaturewith warming
  3. additionAt the end of the addition the majority of material
  4. filtrationThe solids were collected by filtration
  5. washwashed with 2-propanol (3×1 mL)
  6. customdried by suction on the
  7. filtrationfilter

Sources & evidence

ORD record
ord-d08bb69a666e46de92d539c8d9449481
Source dataset
uspto-grants-2009_07
Patent number
US07557247B2

Reaction notes

Loading…