Tetrahydrofuran → HCID 67993137, compound

HRID 449760Notes

Reaction equation

HRID 449760 reaction equation
[CH3:1][O:2][C:3](=[O:42])[C@@H:4]([N:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:28])[C:11]1[CH:16]=[CH:15][C:14]([NH:17]C(OCC2C=CC=CC=2)=O)=[CH:13][CH:12]=1.C1COCC1>[Pd].C(O)(C)C>[CH3:1][O:2][C:3](=[O:42])[CH:4]([N:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:28])[C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67993158HCID 67993158, compound

Product 1

HCID 67993137HCID 67993137, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

10% Pd/C (0.035 g) was added in one portion to a stirred solution of (S)-6-(4-benzyloxycarbonylamino-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 11 (0.350 g, 0.62 mmol) in a 1:1 mixture of THF (5 mL) and isopropanol (5 mL) and nitrogen atmosphere. The reaction mixture was subsequently stiffed under hydrogen atmosphere for 4 h at room temperature. The reaction mixture was passed through a celite pad, and the filtrate was concentrated in under reduced pressure to give (S) 6-(4-amino-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester (12) (0.260 g, 98%) as a white solid.

Workup

  1. concentrationthe filtrate was concentrated in under reduced pressure

Sources & evidence

ORD record
ord-9dcd0ed92bde4f5b9bbd711f4cf785f1
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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