Triphenylphosphine → methyl 4-{[(6-{(2-fluoropropyl)[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate

HRID 1879412Notes

Reaction equation

HRID 1879412 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([S:7]([NH:10][C:11]2[CH:19]=[C:18]3[C:14]([CH2:15][CH2:16][CH2:17]3)=[CH:13][C:12]=2[O:20][CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)(=[O:9])=[O:8])[S:5][CH:6]=1.[F:32][CH:33]([CH3:36])[CH2:34]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:32][CH:33]([CH3:36])[CH2:34][N:10]([S:7]([C:4]1[S:5][CH:6]=[C:2]([CH3:1])[N:3]=1)(=[O:8])=[O:9])[C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][CH2:16][CH2:17]2)=[CH:13][C:12]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 132784572-Fluoropropan-1-olHCID 67106088methyl 4-{[(6-{[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate

Product 1

HCID 58398472methyl 4-{[(6-{(2-fluoropropyl)[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoateYield 103.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

311 mg of methyl 4-{[(6-{[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate, 63.6 mg of 2-fluoro-1-propanol, and 356 mg of triphenylphosphine were dissolved in 4.0 mL of THF, and 591 mg of diethyl azodicarboxylate was added thereto under ice-cooling, followed by stirring at room temperature for 20 hours. The reaction liquid was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 60:40) to obtain 364 mg of methyl 4-{[(6-{(2-fluoropropyl)[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate.

Workup

  1. temperatureunder ice-cooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 60:40)

Sources & evidence

ORD record
ord-07c87d6699234ed4b970da9c26875045
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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