HCID 71622478, compound → HCID 89651722, compound

HRID 2174249Notes

Reaction equation

HRID 2174249 reaction equation
[CH3:1][Mg]Cl.[CH2:4]([NH:6][C:7](=[O:39])[NH:8][C:9]1[CH:31]=[C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](N(OC)C)=[O:25])=[CH:18][CH:17]=2)=[O:14])=[CH:11][N:10]=1)[CH3:5]>C1COCC1>[CH2:4]([NH:6][C:7](=[O:39])[NH:8][C:9]1[CH:31]=[C:30]([NH:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:12]([C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24](=[O:25])[CH3:1])=[CH:20][CH:21]=2)=[O:14])=[CH:11][N:10]=1)[CH3:5]

Participants

4

Reactant 2

HCID 71622478HCID 71622478, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 89651722HCID 89651722, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methylmagnesium chloride (100 μmol, 0.3 mmol) was added to THF (1 mL) and cooled to 0° C. Compound 123 (8 mg, 0.016 mmol) was dissolved in THF (1 mL) and this solution added dropwise to the Grignard at 0° C. The mixture was allowed to warm slowly to RT over 1 h then quenched with NH4Cl and diluted with water and EtOAc. The mixture was extracted into EtOAc and the organics combined and dried with brine then Na2SO4 then evaporated to dryness. The residue was applied to a silica column in DCM (1 mL) and MeOH (2 drops) and eluted with MeOH in DCM to afford Compound 122 (4 mg).

Workup

  1. additionthis solution added dropwise to the Grignard at 0° C
  2. temperatureto warm slowly to RT over 1 h
  3. customthen quenched with NH4Cl
  4. additiondiluted with water and EtOAc
  5. extractionThe mixture was extracted into EtOAc
  6. dry with materialdried with brine
  7. customNa2SO4 then evaporated to dryness
  8. washMeOH (2 drops) and eluted with MeOH in DCM

Sources & evidence

ORD record
ord-3ac86a39cdaa468e9cd5a9fa3ef3cddf
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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