Water → Milveterol

HRID 502001Notes

Reaction equation

HRID 502001 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]Cl.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 24526ChlorineHCID 9892481Milveterol2×

Product 2

HCID 9892481MilveterolYield 67%HCID 11225217Milveterol hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Conditions

Temperature
57.5 °C

Procedure

A 250 mL three-necked flask was charged with a hydrochloride salt of compound 1 having 1.52 equivalents of chlorine per mole of compound 1 (6.1 g, 12 mmol) and 1:1 isopropanol:water (98 mL). The mixture was heated to 50-65 ° C. to dissolve the solid and the solution was stirred at 50-60 ° C. Isopropanol (98 mL) was slowly added over 30 min at 50-60 ° C. and the solution was cooled to room temperature over 3 h. Isopropanol (98 mL) was slowly added over 30 min and the solution was stirred at room temperature for 7h. The crystals were isolated by filtration, washed with isopropanol (30 mL) and dried under vacuum for 16 h to yield the monohydrochloride salt of compound 1 (3.8 g, 8.0 mmol, 67% yield, 99.7% purity by HPLC)

Workup

  1. dissolutionto dissolve the solid
  2. temperaturethe solution was cooled to room temperature over 3 h
  3. stirringthe solution was stirred at room temperature for 7h
  4. customThe crystals were isolated by filtration
  5. washwashed with isopropanol (30 mL)
  6. customdried under vacuum for 16 h

Sources & evidence

ORD record
ord-23ba71e25d8d4cca97bf51815e4d0a2f
Source dataset
uspto-grants-2010_08
Patent number
US07772434B2

Reaction notes

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