Water → t-Butoxycarbonylglycyl thyroxine methyl ester

HRID 279820

Reaktionsgleichung

Reaktionsgleichung von HRID 279820
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([O:5]N1C(=O)CCC1=O)=O.[CH3:20][O:21][C:22](=[O:44])[C@H:23]([CH2:25][C:26]1[CH:33]=[C:31]([I:32])[C:30]([O:34][C:35]2[CH:42]=[C:40]([I:41])[C:39]([OH:43])=[C:37]([I:38])[CH:36]=2)=[C:28]([I:29])[CH:27]=1)[NH2:24].O.C(OCC)(=O)C>CO.CC(C)=O>[CH3:20][O:21][C:22](=[O:44])[C@H:23]([CH2:25][C:26]1[CH:27]=[C:28]([I:29])[C:30]([O:34][C:35]2[CH:36]=[C:37]([I:38])[C:39]([OH:43])=[C:40]([I:41])[CH:42]=2)=[C:31]([I:32])[CH:33]=1)[NH:24][C:3](=[O:5])[CH2:2][NH:1][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 13911218Methyl O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosinate

Produkt 1

HCID 18602701t-Butoxycarbonylglycyl thyroxine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To the aforesaid Boc-Gly-OSu solution the thyroxine methyl ester solution was added while ice cooling. After permitting the same to warm to room temperature, the mixture was stirred for 1.5 hr. After letting the reaction mixture stand overnight, 25 ml. of distilled water and 50 ml. of ethyl acetate were added thereto and the mixture was extracted with ethyl acetate. The extraction was repeated three times using 25 ml. of ethyl acetate. The ethyl acetate layers were combined and dried over anhydrous magnesium sulfate. The liquid was concentrated using a rotary evaporator and subjected to gel chromatography using a column filled with Sephadex LH-20 (made by Pharmacia Co., Ltd.). As the solvent, a mixture obtained by mixing acetone and methanol in a proportion of 4:1 (volume) was used. While confirming by TLC, the objective fraction was taken and concentrated under reduced pressure followed by crystallization. The product was obtained in an amount of 950 mg. (yield 82.5%).

Aufarbeitung

  1. waitstand overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe extraction
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe liquid was concentrated
  6. customa rotary evaporator
  7. additionfilled with Sephadex LH-20 (made by Pharmacia Co., Ltd.)
  8. customAs the solvent, a mixture obtained
  9. concentrationconcentrated under reduced pressure
  10. customfollowed by crystallization
  11. customThe product was obtained in an amount of 950 mg

Quellen und Nachweise

ORD-Eintrag
ord-7ec2364d73ff4c30b447b924255c2d63
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587102

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