Triphenylphosphine → HCID 68601487, compound

HRID 1185597Notes

Reaction equation

HRID 1185597 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:31])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[C:27]([OH:29])[C:26]3[C:21](=[CH:22][C:23]([CH3:30])=[CH:24][CH:25]=3)[N:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:32]([O:39][C:40](=[O:44])[C@H:41]([CH3:43])O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:31])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[C:27]([O:29][C@@H:41]([C:40]([O:39][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:44])[CH3:43])[C:26]3[C:21](=[CH:22][C:23]([CH3:30])=[CH:24][CH:25]=3)[N:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11052238benzyl (2S)-2-hydroxypropanoateHCID 178452377HCID 178452377, compound

Product 1

HCID 68601487HCID 68601487, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6 g 4-{2-[(4-Hydroxy-7-methyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester and 2.5 g benzyl-L-lactate in 97 ml THF were added 5.5 g triphenylphosphine and 3.6 g diethylazodicarboxylate. After stirring for 16 h at RT LCMS indicated complete conversion and water was added to the reaction mixture which was then extracted with ethyl acetate. The residue obtained after evaporation of the solvent was purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 5.5 g

Workup

  1. additionwas added to the reaction mixture which
  2. extractionwas then extracted with ethyl acetate
  3. customThe residue obtained
  4. customafter evaporation of the solvent
  5. customwas purified by flash chromatography on silica using an ethyl acetate/heptane gradient

Sources & evidence

ORD record
ord-08dacfcab2e0441fbdb828bec6661bf3
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

Loading…