HCID 89533759, compound → HCID 89533761, compound

HRID 920266Notes

Reaction equation

HRID 920266 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:2].[CH3:20][Mg]Br>>[OH:2][C@H:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH3:20]

Participants

3

Reactant 2

HCID 89533759HCID 89533759, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 89533761HCID 89533761, compound

Procedure

A solution of 33-5 (0.385 g, 1.462 mmol) in was treated with methylmagnesium bromide (5.1 ml, 15.3 mmol, 3M in diethylether) at 0° C. After stirring overnight at RT, the reaction was quenched with NH4Cl solution. Extracted with Ethyl acetate, washed with brine and dried over sodium sulfate. Material was purified by reverse phase column chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield a white solid. Racemic material was separated by chiral chromatography (ChiralTech IC column) to yield 33-6.

Workup

  1. customthe reaction was quenched with NH4Cl solution
  2. extractionExtracted with Ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customMaterial was purified by reverse phase column chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA)
  6. customto yield a white solid
  7. customRacemic material was separated by chiral chromatography (ChiralTech IC column)
  8. customto yield 33-6

Sources & evidence

ORD record
ord-30465667517546b4ac6ab34403693247
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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