Acetic Acid → HCID 91551587, compound

HRID 1796868Notes

Reaction equation

HRID 1796868 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:21][CH2:22][S:23][CH3:24])[CH:10]([O:14]C1CCCCO1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:21][CH2:22][S:23][CH3:24])[CH:10]([OH:14])[C:11]([O:13][CH3:25])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 69588744HCID 69588744, compound

Product 1

HCID 91551587HCID 91551587, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution of Example 11B (0.25g, 0.68 mmol) and trimethylsilyldiazomethane (2.0M in hexanes, 15 mL) in THF at room temperature was stirred for 4 hours, treated with acetic acid (1 mL), and concentrated. The residue was dissolved in methanol, treated with p-toluenesulfonic acid (10 mg), and heated to 55° C. for 16 hours. The mixture was concentrated and purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes to provide the desired product. MS (APCI(+)) m/e 294 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol
  3. additiontreated with p-toluenesulfonic acid (10 mg)
  4. concentrationThe mixture was concentrated
  5. custompurified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5c530371d07e4c279c5de7fa0eb9c6a9
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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