Hydrochloric Acid → Pioglitazone hydrochloride, (R)-

HRID 882703

反応式

HRID 882703 の反応式
C(O[C@H]([C@H](C(O)=O)OC(=O)C1C=CC=CC=1)C(O)=O)(=O)C1C=CC=CC=1.[CH2:27]([C:29]1[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][O:37][C:38]2[CH:51]=[CH:50][C:41]([CH2:42][C@H:43]3[S:47][C:46](=[O:48])[NH:45][C:44]3=[O:49])=[CH:40][CH:39]=2)=[N:33][CH:34]=1)[CH3:28].[ClH:52]>CO>[ClH:52].[CH2:27]([C:29]1[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][O:37][C:38]2[CH:51]=[CH:50][C:41]([CH2:42][C@H:43]3[S:47][C:46](=[O:48])[NH:45][C:44]3=[O:49])=[CH:40][CH:39]=2)=[N:33][CH:34]=1)[CH3:28]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 53343681(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (-)-O,O'-dibenzoyl-L-tartrate

生成物 1

HCID 53358444Pioglitazone hydrochloride, (R)-

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The product from Example 15, Step 3 was dissolved in MeOH (2.25 mL) containing 37% HCl (0.134 mL) at 35° C. The solution was filtered, EtOAc (9 mL) was poured into the stirred solution and the mixture stirred for 20 min. The white solid was collected by filtration, washed with EtOAc and dried at 30° C. under high vacuum to give the title compound (0.181 g). (Method 1) 98.3%, Rt 10.65 min.; 1.7%, Rt 14.83 min e.e. 96.6%. LCMS (Method 2): Rt 2.90 min 99.39%, m/z 357 [MH+—HCl]. LCMS (Method 3) Rt 2.91 min, m/z 357 [MH+—HCl]. 1H NMR (400 MHz, DMSO-d6): δ 12.0 (1H, s), 8.70 (1H, d, J=1.7 Hz), 8.36 (1H, bd, J=8.3 Hz), 7.93 (1H, d, J=8.2 Hz), 7.15, 6.87 (4H, A2B2q, J=8.7 Hz), 4.86 (1H, dd, J 4.4, 8.9 Hz), 4.38 (2H, t, J=6.3 Hz), 3.44 (2H, t, J=6.2 Hz), 3.29 (1H, dd, J 4.3, 14.2 Hz), 3.06 (1H, dd, J 9.0, 14.3 Hz), 2.78 (2H, q, J=7.6 Hz), 1.23 (3H, t, J=7.6 Hz).

後処理

  1. filtrationThe solution was filtered
  2. additionEtOAc (9 mL) was poured into the stirred solution
  3. filtrationThe white solid was collected by filtration
  4. washwashed with EtOAc
  5. customdried at 30° C. under high vacuum

出典と根拠

ORDレコード
ord-9dddb6dc4625456ab696980c1a6ce6ad
出典データセット
uspto-grants-2012_08
特許番号
US08236786B2

関連ノート

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