Hydrochloric Acid → N-Acetylthyroxine

HRID 265216

반응식

HRID 265216 반응식
[Na+].[NH2:2][C@H:3]([C:23]([O-:25])=[O:24])[CH2:4][C:5]1[CH:12]=[C:10]([I:11])[C:9]([O:13][C:14]2[CH:21]=[C:19]([I:20])[C:18]([OH:22])=[C:16]([I:17])[CH:15]=2)=[C:7]([I:8])[CH:6]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].Cl>[NH4+].[OH-].CN(C=O)C.O.[OH-].[Na+]>[C:26]([NH:2][C@H:3]([C:23]([OH:25])=[O:24])[CH2:4][C:5]1[CH:6]=[C:7]([I:8])[C:9]([O:13][C:14]2[CH:15]=[C:16]([I:17])[C:18]([OH:22])=[C:19]([I:20])[CH:21]=2)=[C:10]([I:11])[CH:12]=1)(=[O:28])[CH3:27]

참가 물질

8

반응물 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 23666112Levothyroxine Sodium

생성물 1

HCID 20638380N-Acetylthyroxine수율 90%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 14798Sodium Hydroxide용매HCID 14923Ammonium Hydroxide용매

실험 절차

L-Thyroxine sodium salt, pentahydrate (1) (10 g, 11 mmol) was nearly completely dissolved in 400 mL of ETCH/2N NH4OH (1/1, v/v), filtered, and filtrate poured into 425 mL of 5% HCl. The resulting precipitate was isolated by vacuum filtration and dried under high vacuum to afford a white solid. This material was dissolved in 160 mL DMF, 100 mL (1.06 mol) of acetic anhydride added, and reaction stirred for 1.5 hours, then diluted with 850 mL H2O and allowed to stand at 4° C. for 16 hours. The resulting precipitate was isolated by filtration, then dissolved in 350 mL EtCH and 41 mL of 1N NaOH, stirred for 2.5 hours, 680 mL of 5% HCl added, and mixture allowed to stand at 4° C. for 16 hours. The resulting precipitate was isolated by vacuum filtration and dried under high vacuum to yield 8.1 g (90%) of the desired N-acetyl L-thyroxine (5) as a white solid; 1H NMR (200 MHz, CD3OD) d 7.8 (s, 2H), 7.1 (s, 2H), 4.6-4.7 (m, 1H), 2.8-3.0 (m, 2H), 2.0 (s, 3H); mass spec (FAB) (M+H)+820.

후처리

  1. filtrationv/v), filtered
  2. additionfiltrate poured into 425 mL of 5% HCl
  3. customThe resulting precipitate was isolated by vacuum filtration
  4. customdried under high vacuum
  5. customto afford a white solid
  6. customreaction
  7. waitto stand at 4° C. for 16 hours
  8. customThe resulting precipitate was isolated by filtration
  9. stirringstirred for 2.5 hours
  10. waitto stand at 4° C. for 16 hours
  11. customThe resulting precipitate was isolated by vacuum filtration
  12. customdried under high vacuum

출처 및 근거

ORD 기록
ord-2f053ae5761b40eca8afc9aa31317f8c
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648272

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