Ethyl Acetate → HCID 86677159, compound

HRID 1429374Notes

Reaction equation

HRID 1429374 reaction equation
N1C2C(=C([S:11]([N:14]3[CH2:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[CH2:18][O:17][CH2:16][C@H:15]3[CH2:26][OH:27])(=[O:13])=[O:12])C=CC=2)C=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].CC(=O)O[CH2:36][CH3:37]>C1COCC1>[CH3:28][S:29]([O:27][CH2:26][C@H:15]1[N:14]([S:11]([C:22]2[CH:23]=[CH:24][CH:25]=[C:37]3[C:36]=2[N:14]=[CH:21][CH:20]=[CH:19]3)(=[O:13])=[O:12])[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[CH2:18][O:17][CH2:16]1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 71269376HCID 71269376, compound

Product 1

HCID 86677159HCID 86677159, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the mixture of compound 15 (200 mg, 0.52 mmol) and TEA (0.2 mL, 1.5 mmol) in THF (25 mL) at rt, methanesulfonyl chloride (71 mg, 0.62 mmol) was added. The resulting mixture was stirred at rt for overnight. The reaction mixture was poured in ice water (100 mL), extracted with EA (3×100 mL). The combined organic layer was washed with water (100 mL) and brine (100 mL), dried over anhydrous Na2SO4. Concentration in vacuo and purified by CC, eluting with PE:EA=2:1 afforded compound 17a as white solid (210 mg, 87% yield).

Workup

  1. extractionextracted with EA (3×100 mL)
  2. washThe combined organic layer was washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationConcentration in vacuo
  5. custompurified by CC
  6. washeluting with PE

Sources & evidence

ORD record
ord-9e4bef7579294ee2bdda3fc43eacce85
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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