Tributylphosphine → Methyl 3-[4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoate

HRID 732217Notes

Reaction equation

HRID 732217 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])=[CH:33][CH:32]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][O:29][C:31]3[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])=[CH:33][CH:32]=3)=[CH:26][CH:27]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 23111783(4-{[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol

Product 1

HCID 23143327Methyl 3-[4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoateYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]phenyl]methanol (409 mg, 0.98 mmol), methyl 3-(4-hydroxyphenyl)propanoate (195 mg, 1.18 mmol) and tributylphosphine (297 mg, 1.47 mmol) in tetrahydrofuran (20 mL) was added 1,1′-(azodicarbonyl)dipiperidine (371 mg, 1.47 mmol), and the mixture was stirred at room temperature for 16 hr. The insoluble materials were filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound (273 mg, yield 50%) as a colorless oil.

Workup

  1. filtrationThe insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-337931731b74471385435c0544822f9e
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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