Hydrochloric Acid → N-Acetylthyroxine

HRID 2294509

反応式

HRID 2294509 の反応式
[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.CCO.[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]

参加物

9

反応物 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 23666112Levothyroxine Sodium

生成物 1

HCID 20638380N-Acetylthyroxine収率 90%

試薬・触媒・溶媒 5

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 14798Sodium Hydroxide溶媒HCID 14923Ammonium Hydroxide溶媒

実験手順

L-Thyroxine sodium salt, pentahydrate (1) (10 g, 11 mmol) was nearly completely dissolved in 400 mL of ETCH/2 N 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 1.60 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 EtOH 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.

後処理

  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. waitto stand at 4° C. for 16 hours
  10. customThe resulting precipitate was isolated by vacuum filtration
  11. customdried under high vacuum

出典と根拠

ORDレコード
ord-2ba69dc8a34244c79b3352a3a0e854b7
出典データセット
uspto-grants-1997_11
特許番号
US05688921

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