3-Bromooxan-2-one → ethyl((1S)-5-{3-[4-(6,7-dihydro-5h-pyrano[2,3-d][1,3]thiazol-2-yl)-2-propylphenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate

HRID 603424Notes

Reaction equation

HRID 603424 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].Br[CH:34]1[CH2:39][CH2:38][CH2:37][O:36][C:35]1=O>CCO>[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]5[CH2:39][CH2:38][CH2:37][O:36][C:35]=5[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 2

HCID 110629723-Bromooxan-2-oneHCID 16110446ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 16110465ethyl((1S)-5-{3-[4-(6,7-dihydro-5h-pyrano[2,3-d][1,3]thiazol-2-yl)-2-propylphenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetateYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (0.5 g, 1.1 mmol) (Example 144) and 3-bromotetrahydro-2H-pyran-2-one (1.2 g, 6.6 mmol) (Example 151) in EtOH (anhydrous, 15 mL) was heated at 70° C. for 18 h. The reaction mixture was cooled to rt, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:2) gave 0.17 g (29%) of the title compound as a light yellow oil. LC-MS: RT=4.52 min, (M+H)+:536.4.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:2)

Sources & evidence

ORD record
ord-a1e49bcc1e2e478d91f501bca7fb6b8a
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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