Ethanol → HCID 68864556, compound

HRID 1725881Notes

Reaction equation

HRID 1725881 reaction equation
N(C(OC(C)(C)C)=O)=NC(O[C:6](C)(C)[CH3:7])=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[C:38]([O:40]C)=[O:39])(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(O)C.[Li+].[OH-]>C1COCC1>[CH2:6]([N:27]([S:24]([C:21]1[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=1)(=[O:25])=[O:26])[C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]=1[C:38]([OH:40])=[O:39])[CH3:7]

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 97268Di-tert-butyl azodicarboxylateHCID 68864942HCID 68864942, compound

Product 1

HCID 68864556HCID 68864556, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Macroporous polystyrene-bound triphenylphosphine resin (56 mg, 0.17 mmol) was treated with di-tert-butyl azodicarboxylate (29 mg, 0.13 mmol) in THF (0.5 mL), shaken at ambient temperature for 15 minutes, treated with a solution of Example 98A (30 mg, 0.08 mmol) in THF (1 mL), shaken at ambient temperature for 15 minutes, treated with ethanol (0.006 mL, 0.11 mmol), shaken for 16 hours at 60° C., filtered, and concentrated. The residue was dissolved in 2:1 dioxane/water (1 mL), treated with LiOH (25 mg, 0.6 mmol), and heated to 160° C. for 30 minutes in a microwave reactor. The reaction mixture was concentrated and purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. MS (DCI) m/e 391 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 7.99 (m, 2H), 7.92 (m, 1H), 7.81 (br s, 2H), 7.64 (br s, 2H), 7.46 (t, 2H), 7.02 (d, 1H), 3.60 (br s, 2H), 0.99 (t, 3H).

Workup

  1. stirringshaken at ambient temperature for 15 minutes
  2. stirringshaken for 16 hours at 60° C.
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 2:1 dioxane/water (1 mL)
  6. temperatureheated to 160° C. for 30 minutes in a microwave reactor
  7. concentrationThe reaction mixture was concentrated
  8. custompurified by C18 reverse-phase

Sources & evidence

ORD record
ord-76905094bc234abd9e372c6549554811
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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