Acetyl chloride → HCID 25183374, compound

HRID 1925699Notes

Reaction equation

HRID 1925699 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])(=[O:13])=[O:12])=[C:7]([OH:23])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>O1CCCC1.C(OCC)(=O)C>[C:31]([O:23][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:10]=[CH:9][C:8]=1[S:11]([NH:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]([OH:22])=[O:21])(=[O:13])=[O:12])(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 25183798HCID 25183798, compound

Product 1

HCID 25183374HCID 25183374, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 35 (137.2 mg; 0.39 mmol) and triethylamine (0.06 mL; 0.46 mmol) in tetrahydrofuran (2 mL) was added acetyl chloride (0.03 mL; 0.46 mmol). After addition was complete, the reaction mixture was stirred at 0° C. for 30 minutes then allowed to warm to room temperature and stirred for 4 hours. The reaction mixture was diluted with ethyl acetate, washed successively with water, aqueous saturated sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes to yield the title compound as a white foam (67.0 mg).

Workup

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. stirringstirred for 4 hours
  4. washwashed successively with water, aqueous saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by automated silica gel column chromatography (Biotage®)
  8. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-dd44afeb9a5e40908d5ddcd3ffcf9a3f
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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