HCID 71145828, compound → HCID 71145623, compound

HRID 536324Notes

Reaction equation

HRID 536324 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH:7]([N:10]2[C:19](=[O:20])[CH2:18][C:17]3[C:12](=[CH:13][C:14]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([O:21][CH3:22])[CH:16]=3)[CH:11]2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:34][Mg]Br>C1COCC1>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH:11]2[C:12]3[C:17](=[CH:16][C:15]([O:21][CH3:22])=[C:14]([O:23][CH:24]([CH3:26])[CH3:25])[CH:13]=3)[CH2:18][C:19](=[O:20])[N:10]2[CH:7]2[CH2:6][CH2:5][CH:4]([C:1]([OH:3])([CH3:34])[CH3:2])[CH2:9][CH2:8]2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 71145828HCID 71145828, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 71145623HCID 71145623, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of Example 15 (100 mg, 0.211 mmol) in THF (1.05 ml) was added methylmagnesium bromide (3M in diethyl ether) (0.126 ml, 0.329 mmol) during 2 min at −15° C. Stirring was continued for 2 h at RT and then quenched with 1M NH4Cl. The mixture was extracted with EtOAc (2×). The organic phases were washed with brine and dried over Na2SO4, filtered and evaporated to dryness. The resulting crude material was purified by reverse phase prep-HPLC (Waters system) to yield the title compound as a beige foam (17 mg, 0.035 mmol, 17%). HPLC: BtRet=5.71; LC-MS: m/z 486.3 [M+H]+.

Workup

  1. customquenched with 1M NH4Cl
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. washThe organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting crude material was purified by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record
ord-d94b4830678b4515a4f3ac36d371dbf8
Source dataset
uspto-grants-2014_10
Patent number
US08859586B2

Reaction notes

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