Diethyl[[4-[2-[(5-t-butyloxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]aminoethyl]-o-phenylene]dioxy]diacetate → tert-butyl 2-formyl-4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate

HRID 1940379Notes

Reaction equation

HRID 1940379 reaction equation
C(C(CC)(OC1C=CC(CCN[C:17]([C:19]2[S:27][C:26]3[CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][C:21]=3[CH:20]=2)=[O:18])=CC=1OCC([O-])=O)C([O-])=O)C.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[C:31]([O:30][C:28]([N:23]1[CH2:24][CH2:25][C:26]2[S:27][C:19]([CH:17]=[O:18])=[CH:20][C:21]=2[CH2:22]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 21466095Diethyl[[4-[2-[(5-t-butyloxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]aminoethyl]-o-phenylene]dioxy]diacetateHCID 178418287HCID 178418287, compound

Product 1

HCID 11845085tert-butyl 2-formyl-4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylateYield 196.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of the compound prepared in (a) (1.2 g) in dichloromethane (20 ml) was added pyridinium chlorochromate (1.1 g), and the mixture was stirred at room temperature for 4 hours. After the reaction mixture was filtered through FLORISIL, the filtrate was concentrated and purified by column chromatography on silica gel to give 1.07 g of the title compound from the fraction eluted with ethyl acetate:n-hexane=1:3 (yield, 89.8%).

Workup

  1. filtrationAfter the reaction mixture was filtered through FLORISIL
  2. concentrationthe filtrate was concentrated
  3. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f7ee7e1f497f450bbaf31e143a244511
Source dataset
uspto-grants-1997_12
Patent number
US05698692

Reaction notes

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