Tributylphosphine → {2-Methyl-4-[3-(3-morpholin-4-yl-propoxy)-5-phenylethynyl-phenylsulfanyl]-phenoxy}-acetic Acid Ethyl Ester

HRID 1513125Notes

Reaction equation

HRID 1513125 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[C:18]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]=[C:16]([OH:28])[CH:15]=2)=[CH:9][C:8]=1[CH3:29])[CH3:2].[N:31]1([CH2:37][CH2:38][CH2:39]O)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[C:18]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]=[C:16]([O:28][CH2:39][CH2:38][CH2:37][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:15]=2)=[CH:9][C:8]=1[CH3:29])[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 1995763-Morpholino-1-propanolHCID 57791909[4-(3-hydroxy-5-phenylethynyl-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

Product 1

HCID 67170534{2-Methyl-4-[3-(3-morpholin-4-yl-propoxy)-5-phenylethynyl-phenylsulfanyl]-phenoxy}-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[4-(3-Hydroxy-5-phenylethynyl-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (0.25 g; 0.60 mmol), 3-morpholin-4-yl-propan-1-ol (0.12 g; 0.84 mmol) and tributylphosphine (0.27 mL; 1.08 mmol) were dissolved in THF (20 mL) in a dried reaction flask under an atmosphere of nitrogen. 1,1′-(Azodicarbonyl)dipiperidine (0.27 g; 1.08 mmol) dissolved in THF (10 mL) was added to the reaction mixture, which was stirred at room temperature for 16 h. The reaction mixture was evaporated to dryness, acetonitrile added, and the mixture filtered. The solution was purified by prep HPLC (method A). Yield: 150 mg. HPLC-MS: m/z: 546.6 (M+H); Rt: 2.08 min.

Workup

  1. additionwas added to the reaction mixture, which
  2. customThe reaction mixture was evaporated to dryness, acetonitrile
  3. additionadded
  4. filtrationthe mixture filtered
  5. customThe solution was purified by prep HPLC (method A)

Sources & evidence

ORD record
ord-33c02f0ab3164366a9f06b03fd6fe5d1
Source dataset
uspto-grants-2012_07
Patent number
US08217086B2

Reaction notes

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