Tributylphosphine → HCID 59729386, compound

HRID 1669297Notes

Reaction equation

HRID 1669297 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[N:26]=[CH:25][C:24]([CH:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28]O)=[CH:23][CH:22]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:28][CH:27]([C:24]2[CH:25]=[N:26][C:21]([Cl:20])=[CH:22][CH:23]=2)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58186708HCID 58186708, compoundHCID 59729434HCID 59729434, compound

Product 1

HCID 59729386HCID 59729386, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(4-hydroxy-benzoylamino)-propionic acid tert-butyl ester (1.17 g, 4.4 mmol) and 2-(6-Chloro-pyridin-3-yl)-octan-1-ol (0.852 g, 3.55 mmol) in toluene (10.0 mL) is degassed and filled with nitrogen for 3 times. Tributylphosphine (1.34 mL, 5.32 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (1.34 g, 5.32 mmol). The reaction mixture is allowed to warm to room temperature and stirred over night, the mixture is loaded on silica gel column. Chromatography gives the title compound (180 mg).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-5fb2d4fb830a4b0db71ee03e9428e9d3
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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