Sodium Chloride → N-Trifluoroacetylthyroxine

HRID 28066

반응식

HRID 28066 반응식
[NH2:1][C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][C:4]1[CH:11]=[C:9]([I:10])[C:8]([O:12][C:13]2[CH:20]=[C:18]([I:19])[C:17]([OH:21])=[C:15]([I:16])[CH:14]=2)=[C:6]([I:7])[CH:5]=1.[F:25][C:26]([F:31])([F:30])[C:27](O)=[O:28].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl-].[Na+]>C(OCC)(=O)C.O>[F:25][C:26]([F:31])([F:30])[C:27]([NH:1][C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][C:4]1[CH:5]=[C:6]([I:7])[C:8]([O:12][C:13]2[CH:14]=[C:15]([I:16])[C:17]([OH:21])=[C:18]([I:19])[CH:20]=2)=[C:9]([I:10])[CH:11]=1)=[O:28]

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 5819ThyroxineHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydride

생성물 1

HCID 12831641N-Trifluoroacetylthyroxine

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 20 g [25.6 millimoles (mmol)] of L-thyroxine (Sigma Chemical Co., St. Louis, Missouri USA) in 240 ml of dry ethyl acetate containing 46 ml of trifluoroacetic acid and 7.6 ml of trifluoroacetic anhydride was stirred at 0° C. for one hour. Upon warming to room temperature and adding 200 ml of H2O, a suspension formed which was then saturated with sodium chloride. The organic phase of the mixture was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to give 21.3 g of the N-protected thyroxine derivative (6). A sample was recrystallized from ether-pentane to give fine crystals, m.p. 233°-235° C. (decomposed).

후처리

  1. customa suspension formed which
  2. customThe organic phase of the mixture was separated
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-f4ae88b632384fb39c042a98dcafd60c
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04225485

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