m-Chloroperbenzoic acid → tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4',3':4,5]thieno(2,3-b]pyridin-4-yl}phenoxy)-acetate

HRID 481125Notes

Reaction equation

HRID 481125 reaction equation
[Cl:1][C:2]1[C:3]([C:23]2[CH:37]=[CH:36][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:25][CH:24]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][S:21][CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].ClC1C=CC=C(C(OO)=[O:46])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:23]2[CH:37]=[CH:36][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[CH:25][CH:24]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][S:21](=[O:46])[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:10](=[O:15])[CH2:11][CH2:12][C:13]1=[O:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86588675tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-5,8-dihydro-6H-thiopyrano[4',3':4,5]-thieno[2,3-b]pyridin-4-yl}phenoxy)acetate

Product 1

HCID 86588674tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4',3':4,5]thieno(2,3-b]pyridin-4-yl}phenoxy)-acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Example 112 (2.7 g) in methylene chloride (50 ml) was added m-chloroperbenzoic acid (70%, 1.2 g) under ice-cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and then water and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain tert-butyl (4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4′,3′:4,5]thieno(2,3-b]pyridin-4-yl}phenoxy)-acetate from the fraction eluted with ethyl acetate. It was recrystallized from ethyl acetate-hexane (2.2 g, 79%). Colorless prisms. Melting point 175-176° C.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution
  3. dry with materialwater and dried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a4ce28ff7164f88bc1dbb8b18637635
Source dataset
uspto-grants-2003_11
Patent number
US06653476B2

Reaction notes

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