Triphenylphosphine → HCID 117667179, compound

HRID 712767Notes

Reaction equation

HRID 712767 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([OH:24])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[CH2:26][CH2:27][N:28]1[CH2:32][CH2:31][O:30][C:29]1=[O:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][O:30][C:29]4=[O:33])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-HCID 97268Di-tert-butyl azodicarboxylateHCID 1176672421,1-Dimethylethyl 3,4-dihydro-6-(5-hydroxy-3-pyridinyl)-1,8-naphthyridine-1(2H)-carboxylate

Product 1

HCID 117667179HCID 117667179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

6-(5-Hydroxy-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (100 mg, 0.305 mmol) is dissolved in 2 mL DMF and added to 3-(2-hydroxy-ethyl)-oxazolidin-2-one (48 mg, 0.37 mmol). Triphenylphosphine (192 mg, 0.733 mmol) in 1 mL DMF is added followed by di-t-butyl azodicarboxylate (168 mg, 0.733 mmol) in 1 mL DMF. The solution is shaken at room temperature for 16 hrs. The reaction mixture is evaporated to dryness to afford the crude product. Purification by HPLC chromatography affords 6-{5-[2-(2-oxo-oxazolidin-3-yl)-ethoxy]-pyridin-3-yl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customto afford the crude product
  3. customPurification by HPLC chromatography

Sources & evidence

ORD record
ord-1ab4f44e43c64016839f9df383c52804
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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