Tributylphosphine → HCID 67485984, compound

HRID 658315Notes

Reaction equation

HRID 658315 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH2:11]([O:13][C:14](=[O:32])[CH2:15][CH2:16][NH:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]([CH2:29]O)[CH:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=1)[CH3:12].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH2:11]([O:13][C:14](=[O:32])[CH2:15][CH2:16][NH:17][C:18](=[O:31])[C:19]1[CH:20]=[CH:21][C:22]([CH:25]([CH2:29][O:9][C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:10])[CH:4]=2)[CH:26]([CH3:27])[CH3:28])=[CH:23][CH:24]=1)[CH3:12]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 819704-Bromo-3,5-dimethylphenolHCID 67486312HCID 67486312, compound

Product 1

HCID 67485984HCID 67485984, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-3,5-dimethyl-phenol (818 mg, 4.07 mmol) and 3-[4-(1-hydroxymethyl-2-methyl-propyl)-benzoylamino]-propionic acid ethyl ester (1.0 g, 3.26 mmol) in anhydrous toluene (15 mL) is degassed and filled with nitrogen 3 times. Tributylphosphine (1.21 mL, 4.89 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (1.23 g, 4.89 mmol). The reaction mixture is allowed to warm to room temperature and stirred overnight. The mixture is loaded on a silica gel column and purified using hexanes/ethyl acetate. MS (ES): 488.2 [M+H]−.

Workup

  1. additionfilled with nitrogen 3 times
  2. custompurified

Sources & evidence

ORD record
ord-1eba1351470c4317801afa63f4ec304a
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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