Water → Milveterol

HRID 226285Notes

Reaction equation

HRID 226285 reaction equation
[OH:1][C@H:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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:26])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([NH:23][CH:24]=[O:25])[CH:17]=2)=[CH:7][CH:6]=1.[Cl-:33].[NH4+].O>C(O)(C)C>[ClH:33].[OH:1][C@H:2]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=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:26])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([NH:23][CH:24]=[O:25])[CH:17]=2)=[CH:7][CH:6]=1.[OH:1][C@H:2]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=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:26])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([NH:23][CH:24]=[O:25])[CH:17]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 9892481Milveterol

Product 2

HCID 9892481MilveterolYield 12%HCID 11225217Milveterol hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 200 mL roundbottom flask, compound 1 (200 mg, 0.46 mmol) was dissolved in 40 mL isopropyl alcohol. The solution was stirred and vortexed at room temperature until it became homogeneous. A 7% (w/w) solution of ammonium chloride in water (20 mL, 26 mmol)) was then added dropwise to the stirring solution. The stirring was stopped and the solution was permitted to stand at room temperature for 20 h. White crystals formed. The crystals were collected on a Büchner funnel, washed with 1:1 isopropanol:water (3 mL), and dried for 30 minutes. The crystals were collected to yield the monohydrochloride salt of compound 1 (27 mg, 12% yield).

Workup

  1. customvortexed at room temperature until it
  2. customWhite crystals formed
  3. customThe crystals were collected on a Büchner funnel
  4. washwashed with 1:1 isopropanol
  5. dry with materialwater (3 mL), and dried for 30 minutes
  6. customThe crystals were collected

Sources & evidence

ORD record
ord-4d7b8181faee4ba8b053ec80d3779f78
Source dataset
uspto-grants-2009_07
Patent number
US07557247B2

Reaction notes

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