Tributylphosphine → HCID 23157339, compound

HRID 508069Notes

Reaction equation

HRID 508069 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([OH:23])=[CH:18][C:17]=3[CH3:24])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].[CH3:32][O:33][C:34]1[CH:38]=[C:37]([CH2:39]O)[N:36]([CH3:41])[N:35]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:17]([CH3:24])=[CH:18][C:19]([O:23][CH2:39][C:37]4[N:36]([CH3:41])[N:35]=[C:34]([O:33][CH3:32])[CH:38]=4)=[CH:20][C:21]=3[CH3:22])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23157311HCID 23157311, compoundHCID 23157575Ethyl 3-(2-fluoro-4-{[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate

Product 1

HCID 23157339HCID 23157339, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(2-fluoro-4-{[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate (0.50 g, 1.2 mmol), (3-methoxy-1-methyl-1H-pyrazol-5-yl)methanol (0.17 g, 1.2 mmol) and tributylphosphine (0.59 mL, 2.4 mmol) in tetrahydrofuran (30 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.60 g, 2.4 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, diisopropyl ether was added to the residue, and the resultant insoluble material was filtered off. The filtrate was concentrated and the residue was purified by silica gel column chromatography (40% ethyl acetate/hexane) to give the title compound (0.44 g, yield 68%) as a colorless oil.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiisopropyl ether was added to the residue
  3. filtrationthe resultant insoluble material was filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d226ed98a0cb4cefa14d24648fc0d158
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…