Tributylphosphine → HCID 86615985, compound

HRID 1914299Notes

Reaction equation

HRID 1914299 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][NH:6][C:7](=[O:22])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:21])[CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:10][CH:9]=1.[Cl:24][C:25]1[N:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1.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:23])[CH2:4][CH2:5][NH:6][C:7](=[O:22])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:21][C:28]2[CH:29]=[N:30][C:25]([Cl:24])=[CH:26][CH:27]=2)[CH2:15][CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 8198212-Chloro-5-hydroxypyridineHCID 59518064HCID 59518064, compound

Product 1

HCID 86615985HCID 86615985, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-[4-(1-Hydroxy-4,4-dimethyl-pentyl)-benzoylamino]-propionic acid methyl ester (546 mg, 1.7 mmol) and 6-chloro-pyridin-3-ol (270 mg, 2.09 mmol) are combined in anhydrous toluene (10 mL), degassed, filled with nitrogen for 3 times, and cooled in an ice bath. Tributylphosphine (TBP) (630 uL, 2.55 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (ADDP) (643 mg, 2.55 mmol). The reaction mixture is allowed to warm to room temperature and stirred over night, the mixture is loaded on silica gel column. Chromatography gave the title compound (722 mg, 1.67 mmol).

Workup

  1. customdegassed
  2. additionfilled with nitrogen for 3 times
  3. temperaturecooled in an ice bath

Sources & evidence

ORD record
ord-ad8e7b5ea2334f429478567ae67a1309
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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