HCID 53757231, compound → HCID 53700152, compound

HRID 1004302Notes

Reaction equation

HRID 1004302 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7]=[C:8]([C:25]1[S:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][NH:18][C:17]=2[N:16]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO.C(O)C>[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([C:25]1[S:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][NH:18][C:17]=2[N:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 53757231HCID 53757231, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53700152HCID 53700152, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a stirred suspension of 10% palladium on carbon (50 mg) in methanol (5 mL) was added a solution of 3-(benzothiazol-2-yl)-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-non-2-enoic acidtert-butyl ester 29-7c (190 mg) in ethanol (5 mL) and the mixture was subjected to an atmosphere of hydrogen for 48 hours. The reaction mixture was filtered through Celite and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography over silica gel with 4:1 hexanes/acetone to give 29-8c as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated at reduced pressure
  3. customThe resulting oil was purified by flash column chromatography over silica gel with 4:1 hexanes/acetone

Sources & evidence

ORD record
ord-7812c17632d04b169980eb5d6dcbac98
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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