Pivaloyl chloride → HCID 131723722, compound

HRID 2300954Notes

Reaction equation

HRID 2300954 reaction equation
C1([NH:7][C:8](=[O:30])[C:9]2[CH:14]=[C:13]([OH:15])[C:12]([OH:16])=[CH:11][C:10]=2NC(C2SC3C=CC=CC=3C=2Cl)=O)C=CC=CC=1.[CH3:31][C:32]([CH3:37])([CH3:36])[C:33](Cl)=[O:34]>C(Cl)Cl.N1C=CC=CC=1>[OH:15][C:13]1[C:12]([O:16][C:33]([C:32]([CH3:37])([CH3:36])[CH3:31])=[O:34])=[CH:11][CH:10]=[C:9]([CH:14]=1)[C:8]([NH2:7])=[O:30]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 18377030HCID 18377030, compound

Product 1

HCID 131723722HCID 131723722, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-phenyl-2-[((3-chlorobenzo[b]thien-2-yl)carbonyl)amino]4,5-dihydroxybenzamide (0.09 g, 0.21 mmol) in CH2Cl2 (1 mL) and pyridine (1 mL) at 0° C. was added trimethylacetyl chloride (0.027 mL, 0.22 mmol). The solution was allowed to warm to ambient temperature with stirring. After 16 hours, the reaction mixture was partitioned between ethyl acetate and dilute HCl. The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel to afford 0.038 g (40% yield) of N-phenyl-2-[((3-chlorobenzo b]thien-2-yl)carbonyl)amino]-5-hydroxy4-((1,1-dimethylethyl)carbonyl)oxybenzamide as a white solid; NMR(DMSO-d6) 12.2 (s, 1), 10.8 (s, 1), 10.4 (s, 1), 8.3 (s, 1), 8.2 (d, 1), 8.0 (d, 1), 7.6-7.7 (m, 4), 7.4 (t, 2), 7.1 (t, 1), 1.3 (s, 9) ppm.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and dilute HCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting oil was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-60e8ce65d7a54444ae5844f379b87358
Source dataset
uspto-grants-2002_12
Patent number
US06498185B1

Reaction notes

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