Triphenylphosphine → 2-{4-Methoxy-3-[2-(3-methylsulfanyl-phenyl)-ethoxy]-benzoylamino}-indane-2-carboxylic acid methyl ester

HRID 2405211Notes

Reaction equation

HRID 2405211 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][S:46][C:47]1[CH:48]=[C:49]([CH2:53][CH2:54]O)[CH:50]=[CH:51][CH:52]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:54][CH2:53][C:49]3[CH:50]=[CH:51][CH:52]=[C:47]([S:46][CH3:45])[CH:48]=3)[CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 545382452-(3-(Methylthio)phenyl)ethanolHCID 670765182-(3-Hydroxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

Product 1

HCID 670766102-{4-Methoxy-3-[2-(3-methylsulfanyl-phenyl)-ethoxy]-benzoylamino}-indane-2-carboxylic acid methyl esterYield 39.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of step 2 (0.380 g, 1.11 mmol) and triphenylphosphine (0.461 g, 1.67 mmol) were dissolved in THF. 2-(3-Methylsulfanyl-phenyl)-ethanol (0.281 g, 1.67 mmol) and DIAD (0.359 g, 1.67 mmol) were added and the reaction mixture was stirred at room temperature for 2 h. The volatiles were evaporated in vacuo and the residue was purified by preparative RP HPLC (water/ACN gradient) to give 0.217 g of the title compound.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-47b78f589be64eeb81f6fbb1a9fdbbdc
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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