Isopropanol → HCID 58554766, compound

HRID 449768Notes

Reaction equation

HRID 449768 reaction equation
[CH:1]1[C:13]2[N:12]([C@@H:14]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH2:31][O:32][C:33](=[O:51])[C:34]3[CH:39]=[CH:38][C:37]([NH:40]C(OCC4C=CC=CC=4)=O)=[CH:36][CH:35]=3)=[O:28])[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>[NH2:40][C:37]1[CH:36]=[CH:35][C:34]([C:33]([O:32][CH2:31][CH2:30][O:29][C:27](=[O:28])[CH2:26][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:51])=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 58554730HCID 58554730, compound

Product 1

HCID 58554766HCID 58554766, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on charcoal (0.140 g) was added in one portion to a stirred solution of 24 (0.70 g, 1.02 mmol) in 1:1 mixture of isopropanol (10 mL) and THF (10 mL) under nitrogen atmosphere. The suspension was then stirred under hydrogen atmosphere at room temperature for 4 h. The solution was filtered through celite and concentrated under reduced pressure to obtain (S)-5-(2-(4-aminobenzoyloxy)ethoxy)-2-(9H-carbazol-9-yl)-5-oxopentanoic acid 25 (0.45 g, 96%) as a white solid.

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed45330afb34431e9cdf4b1524ca6545
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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