Isopropanol → HCID 58554732, compound

HRID 449764Notes

Reaction equation

HRID 449764 reaction equation
[CH:1]1[C:13]2[N:12]([C@@H:14]([CH2:25][C:26]([O:28][CH2:29][CH2:30][O:31][C:32](=[O:50])[C:33]3[CH:38]=[CH:37][C:36]([NH:39]C(OCC4C=CC=CC=4)=O)=[CH:35][CH:34]=3)=[O:27])[C:15]([O:17]CC3C=CC=CC=3)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)(C)C>[Pd].C1COCC1>[NH2:39][C:36]1[CH:35]=[CH:34][C:33]([C:32]([O:31][CH2:30][CH2:29][O:28][C:26](=[O:27])[CH2:25][C@H:14]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[C:15]([OH:17])=[O:16])=[O:50])=[CH:38][CH:37]=1

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 67993122HCID 67993122, compound

Product 1

HCID 58554732HCID 58554732, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on charcoal (0.040 g) was added in one portion to a stirred solution of 18 (0.360 g, 0.57 mmol) in a 1:1 mixture of isopropanol (4 mL) and THF (4 mL) under nitrogen atmosphere. The suspension was then stirred under hydrogen atmosphere for 6 h. The solution was filtered through celite and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography CH3OH:CH2Cl2 (5:95) to afford to obtain (S)-4-(2-(4-aminobenzoyloxy)ethoxy)-2-(9H-carbazol-9-yl)-4-oxobutanoic acid 19 (0.230 g, 96%) as a white solid.

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash silica gel column chromatography CH3OH:CH2Cl2 (5:95)
  4. customto afford

Sources & evidence

ORD record
ord-97cf79a4a89d4b049fb82f7dc05fb817
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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