Cesium carbonate → ethyl ((1S)-5-{3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate

HRID 2235900ノート

反応式

HRID 2235900 の反応式
[OH:1][C:2]1[CH:27]=[C:26]([C:28]2[S:29][C:30]3[CH2:36][CH2:35][CH2:34][CH2:33][C:31]=3[N:32]=2)[CH:25]=[CH:24][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C@H:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:13][CH2:12]2.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:44][CH2:45][CH3:46]>CN(C=O)C.O>[CH2:44]([O:1][C:2]1[CH:27]=[C:26]([C:28]2[S:29][C:30]3[CH2:36][CH2:35][CH2:34][CH2:33][C:31]=3[N:32]=2)[CH:25]=[CH:24][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C@H:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:13][CH2:12]2)[CH2:45][CH3:46]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 59300497ethyl ((1S)-5-{3-[2-hydroxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

生成物 1

HCID 59300423ethyl ((1S)-5-{3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate収率 91.2%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 6228Dimethylformamide溶媒

実験手順

Ethyl ((1S)-5-{3-[2-hydroxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)-phenoxy]-propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 165, 90 mg, 0.177 mmol) was dissolved in DMF (3 mL) after which Cs2CO3 (69.3 mg, 0.213 mmol) and water (3 drops) were added. Iodopropane (0.02 mL, 0.213 mmol) was added to the flask, and the reaction mixture was stirred at room temperature for 18 h. The mixture was then filtered and the filtrate purified by preparative HPLC giving the desired ester as a white solid (88.7 mg, 91%). 1H NMR (400 MHz, CD2Cl2): δ 7.47 (s, 1H), 7.37 (dd, 1H), 7.05 (d, 1H), 6.93 (d, 1H), 6.79 (s, 1H), 6.71 (dd, 1H), 4.23 (t, 2H), 4.19-4.13 (m, 4H), 4.03 (t, 2H), 3.50 (m, 1H), 2.94-2.78 (m, 6H), 2.70 (dd, 1H), 2.44-2.25 (m, 4H), 1.92-1.70 (m, 7H), 1.28 (t, 3H), 1.07 (t, 3H).

後処理

  1. additionwere added
  2. filtrationThe mixture was then filtered
  3. customthe filtrate purified by preparative HPLC

出典と根拠

ORDレコード
ord-c7200d6ade6f4ce6a9c4709c7d5cfda5
出典データセット
uspto-grants-2010_05
特許番号
US07714004B2

反応ノート

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