Acetic Acid → HCID 57530038, compound

HRID 1454223Notes

Reaction equation

HRID 1454223 reaction equation
C(O[C:4](=[O:19])[CH2:5][C:6]1[N:11](C)[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8](=[O:18])(=[O:17])[CH:7]=1)C.[H-].[Na+].N#N.Cl.[CH3:25][C:26]([OH:28])=O>C1COCC1>[O:18]=[S:8]1(=[O:17])[C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[NH:11][C:6]([C:5]2[C:4](=[O:19])[NH:11][C:6]([CH3:5])=[C:25]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:10]=3)[C:26]=2[OH:28])=[CH:7]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 947NitrogenHCID 24758Sodium hydrideHCID 68841166HCID 68841166, compound

Product 1

HCID 57530038HCID 57530038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

step 3—To a solution of 76b (91 mg, 0.33 mmol), 4 (89 mg, 0.33 mmol) and THF (3.5 mL) was added in one portion NaH (26 mg, 0.66 mmol) was then added in one portion. After the evolution of N2 subsided the flask was fitted with a reflux condenser, and heated to 80° C. under a N2 atmosphere. The reaction was subsequently monitored by LCMS. When 76b was not longer detectable by hplc the reaction was cooled to RT and glacial HOAc (500 μL) and 1 N HCl (5.0 mL) were added sequentially. The aqueous phase was then extracted with Et2O (3×50 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated. The crude was then purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (25-40% EtOAc) to afford 61 mg (41%) of III-1 as a yellow semi-solid: LCMS RT 2.34 min, [M−H].

Workup

  1. additionwas then added in one portion
  2. customwas fitted with a reflux condenser
  3. temperaturewas cooled to RT
  4. extractionThe aqueous phase was then extracted with Et2O (3×50 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified by SiO2 chromatography
  9. washeluting with a EtOAc/hexane gradient (25-40% EtOAc)
  10. customto afford 61 mg (41%) of III-1 as a yellow semi-solid

Sources & evidence

ORD record
ord-5e224f347c3c4cdfbb807225af1bcc3c
Source dataset
uspto-grants-2009_01
Patent number
US07479489B2

Reaction notes

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