Acetyl chloride → HCID 20078945, compound

HRID 1109971Notes

Reaction equation

HRID 1109971 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([O:12][CH:13]2[CH:17]([OH:18])[CH2:16][O:15][CH2:14]2)=[O:11])=[CH:6][C:5]([N:19]2[C:23](=[O:24])[C:22]3[CH2:25][CH2:26][CH2:27][CH2:28][C:21]=3[C:20]2=[O:29])=[C:4]([F:30])[CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C1C=CC=CC=1>[C:38]([O:18][CH:17]1[CH2:16][O:15][CH2:14][CH:13]1[O:12][C:10]([CH2:9][O:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:30])=[C:5]([N:19]2[C:20](=[O:29])[C:21]3[CH2:28][CH2:27][CH2:26][CH2:25][C:22]=3[C:23]2=[O:24])[CH:6]=1)=[O:11])(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15789768HCID 15789768, compound

Product 1

HCID 20078945HCID 20078945, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In 15 ml of benzene were dissolved 0.66 g of N-(4-chloro-2-fluoro-5-(4-hydroxytetrahydrofuran-3-yloxycarbonylmethoxy)phenyl)-3,4,5,6-tetrahydrophthalimide and 0.20 g of triethylamine, followed by dropwise addition of a solution of 0.14 g of acetyl chloride in benzene. After stirring at room temperature for 4 hours, the reaction mixture was washed with water and subsequently with aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=2/3), to obtain 0.55 g of a compound described in Table 1 (No.3) (76 %).

Workup

  1. washthe reaction mixture was washed with water and subsequently with aqueous saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent
  4. customthe residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=2/3)

Sources & evidence

ORD record
ord-b818a5510bcc41a390b19d38c97aad04
Source dataset
uspto-grants-1994_06
Patent number
US05324709

Reaction notes

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