Ethanol → ethyl 2-[4-(3-{[(1S)-1-(2-ethoxy-2-oxoethyl)-2,3-dihydro-1H-inden-5-yl]oxy}propoxy)-3-propylphenyl]-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate

HRID 2235896Notes

Reaction equation

HRID 2235896 reaction equation
[NH2:1][C:2]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]3)=[C:6]([CH2:30][CH2:31][CH3:32])[CH:5]=1)=[S:3].Cl[CH:34]1[C:38](=O)[CH2:37][O:36][C:35]1=[O:40].[CH3:41][CH2:42][OH:43]>>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C@H:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][C:7]3[CH:28]=[CH:29][C:4]([C:2]4[S:3][C:34]([C:35]([O:36][CH2:37][CH3:38])=[O:40])=[C:41]([CH2:42][OH:43])[N:1]=4)=[CH:5][C:6]=3[CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1)[CH3:27]

Participants

4

Reactant 3

HCID 702EthanolHCID 41585753-Chloro-2,4(3H,5H)-furandioneHCID 16110446ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 59300526ethyl 2-[4-(3-{[(1S)-1-(2-ethoxy-2-oxoethyl)-2,3-dihydro-1H-inden-5-yl]oxy}propoxy)-3-propylphenyl]-4-(hydroxymethyl)-1,3-thiazole-5-carboxylateYield 33%

Conditions

Temperature
70 °C

Procedure

Ethyl ((1S)-5-{3-[4-aminocarbonothioyl)-2-propylphenoxy]propoxy}2,3-dihydro-1H-inden-1-yl)acetate (90 mg, 0.2 mmol) (Example 144) and 3-chloro-2,4(3H, 5H)-furandione (106 mg, 0.8 mmol) were dissolved in EtOH (anhydrous, 8 mL), and the mixture was heated at 70° C. for 18 h. The reaction was cooled to rt, and then concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:1) gave 38 mg (33%) of the btle compound as a clear oil. LC-MS: RT=4.38 min; (M+H)+ 582.3.

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customPurification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:1)

Sources & evidence

ORD record
ord-37d0e6e0effc410b9421feb9fe971808
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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