Triphenylphosphine → HCID 136337340, compound

HRID 1669372Notes

Reaction equation

HRID 1669372 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:21])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1.[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31]O)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:21])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:31][CH2:30][NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 136344249HCID 136344249, compound

Product 1

HCID 136337340HCID 136337340, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 200 mg of 4-hydroxy-3-[3-(3-hydroxyphenyl)-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone, 10 ml of tetrahydrofuran, 170 mg of N-(t-butoxycarbonyl)-2-aminoethanol and 276 mg of triphenylphosphine was added dropwise 414 μl of diethyl azodicarboxylate (40% toluene solution), and this was stirred at room temperature for 47 hours. The solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 75 mg of 4-hydroxy-3-[3-[3-[N-(t-butoxycarbonyl)-2-aminoethoxy]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (54a)].

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3c98c23223bf4d8a8e45805f4bce827c
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

Loading…