Carbonate Ion → Pioglitazone, (R)-

HRID 882701

反応式

HRID 882701 の反応式
C(=O)([O-])[O-].FC(F)(F)C(O)=O.[CH2:12]([C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]([CH2:27][C@H:28]3[S:32][C:31](=[O:33])[NH:30][C:29]3=[O:34])=[CH:25][CH:24]=2)=[N:18][CH:19]=1)[CH3:13]>CO>[CH2:12]([C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]([CH2:27][C@H:28]3[S:32][C:31](=[O:33])[NH:30][C:29]3=[O:34])=[CH:25][CH:24]=2)=[N:18][CH:19]=1)[CH3:13]

参加物

4

反応物 2

HCID 19660Carbonate IonHCID 86651732(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione trifluoroacetate

生成物 1

HCID 29010894Pioglitazone, (R)-収率 47%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

MP-Carbonate (389 mg, 1.06 mmol) was added to a solution of (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione trifluoroacetate (100 mg, 0.21 mmol) in MeOH (100 mL) and stirred at RT for 2 h. The reaction was decanted to leave the resin which was washed with MeOH (3×10 mL) and the combined MeOH fractions were removed in vacuo to afford the title compound (35 mg, 47%). e.e. (Method 10) 92.90%, Rt 6.27 min. 1H NMR (400 MHz, DMSO-d6): δ 12.44-11.11 (1H, bs), 8.34-8.29 (1H, d, J 1.9), 7.55-7.49 (1H, dd, J 2.2, 7.9), 7.24-7.20 (1H, d, J 7.8), 7.12-7.05 (2H, d, J 8.6), 6.84-6.77 (2H, d, J 8.6), 4.78-4.71 (1H, dd, J 4.3, 9.1), 4.30-4.19 (1H, d, J 4.3), 3.24-3.18 (2H, d), 3.11-3.03 (2H, t, J 6.6), 3.00-2.92 (1H, dd, J 9.2, 14.2), 2.59-2.50 (2H, q, J 7.6), 1.17-1.09 (3H, t, J 7.7).

後処理

  1. customThe reaction was decanted
  2. customto leave the resin which
  3. washwas washed with MeOH (3×10 mL)
  4. customthe combined MeOH fractions were removed in vacuo

出典と根拠

ORDレコード
ord-9ee5640700df420d9015ffe40f1328c3
出典データセット
uspto-grants-2012_08
特許番号
US08236786B2

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