Hydrochloric Acid → Pioglitazone hydrochloride, (R)-

HRID 1522794노트

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HRID 1522794 반응식
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]

참가 물질

4

반응물 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

생성물 1

HCID 53358444Pioglitazone hydrochloride, (R)-

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9ed43466142042b6867b99d5fb397081
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09078885B2

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