HCID 68864168, compound → HCID 68863545, compound

HRID 1725886Notes

Reaction equation

HRID 1725886 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][C:15](=[O:22])[C:14]=3[C:13]=2[C:23]([OH:25])=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:26][Mg]Br>C(OCC)C.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][C:15]([OH:22])([CH3:26])[C:14]=3[C:13]=2[C:23]([OH:25])=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 68864168HCID 68864168, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68863545HCID 68863545, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of Example 103B (40 mg, 0.11 mmol) in diethyl ether (3 mL) and THF (2 mL) was treated with methylmagnesium bromide (3M solution in diethyl ether, 0.11 mL), stirred at 45° C. for 2 hours, quenched with saturated NH4Cl, and partitioned between diethyl ether and brine. The organic phase was dried (Na2SO4), filtered, concentrated, and purified by reverse-phase HPLC to provide the desired product. MS (ESI) m/e 378 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 12.18 (br s, 1H), 8.5 (s, 1H), 7.75 (m, 2H), 7.52 (m, 2H), 7.32 (d, 1H), 6.85 (d, 1H), 2.56 (m, 2H), 1.82-1.73 (m, 1H), 1.72-1.61 (m, 1H), 1.53-1.37 (m, 2H), 1.33 (s, 3H).

Workup

  1. customquenched with saturated NH4Cl
  2. custompartitioned between diethyl ether and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-65a5504b1fe54e3fb5c7f36329c2abeb
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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