Tributylphosphine → 3-{4-[1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl ester

HRID 1669330Notes

Reaction equation

HRID 1669330 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24](O)[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:19]=1[CH3:32].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:24]([C:21]2[CH:22]=[CH:23][C:18]([Br:17])=[C:19]([CH3:32])[CH:20]=2)[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 106328533-(4-Hydroxy-benzoylamino)-propionic acid methyl esterHCID 673450331-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-ol

Product 1

HCID 673419823-{4-[1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (805 mg, 3.61 mmol) and 1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-ol (824 mg, 2.89 mmol) in toluene (15.0 mL) was degassed and filled with nitrogen for 3 times. Tributylphosphine (1.1 mL, 4.33 mmol) was added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (1.1 g, 4.33 mmol). The reaction mixture was allowed to warm to room temperature and stirred over night, the mixture was loaded on silica gel column. Chromatography gave the title compound (890 mg, 1.82 mmol).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-66cc52cc37704c038a0a0c6c7c1ff829
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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