N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → t-Butoxycarbonylglycyl thyroxine methyl ester

HRID 622335

反応式

HRID 622335 の反応式
[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>[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]

参加物

4

反応物 2

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

生成物 1

HCID 18602701t-Butoxycarbonylglycyl thyroxine methyl ester収率 82.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To the Boc-Gly-OSu solution was added under ice-cooling the thyroxine methyl ester solution. The resulting mixture was allowed to stand to reach room temperature, and then stirred for 1.5 hrs. The reaction liquid was allowed to stand overnight, and to this were added 25 ml. of distilled water and 50 ml. of ethyl acetate for extraction with the ethyl acetate. The extraction with 25 ml. of ethyl acetate was repeated three times. The ethyl acetate extracts were combined and dried over anhydrous magnesium sulfate. The dry extract was concentrated in a rotary evaporator and subjected to gel chromatography using a column filled with Sephadex LH-20 (tradename of Pharmacia Corp.). In this procedure, a mixture of acetone and methanol in a volume ratio of 4:1 was employed as the developing solvent. Under confirmation by TLC, the fractions containing the desired product were collected and concentrated under reduced pressure to obtain a crystalline product. There was obtained 950 mg. (yield 82.5%) of the desired product.

後処理

  1. customto reach room temperature
  2. customThe reaction liquid
  3. waitto stand overnight
  4. additionto this were added 25 ml
  5. extractionof ethyl acetate for extraction with the ethyl acetate
  6. extractionThe extraction with 25 ml
  7. dry with materialdried over anhydrous magnesium sulfate
  8. extractionThe dry extract
  9. concentrationwas concentrated in a rotary evaporator
  10. additionfilled with Sephadex
  11. additionIn this procedure, a mixture of acetone and methanol in a volume ratio of 4:1
  12. additionUnder confirmation by TLC, the fractions containing the desired product
  13. customwere collected
  14. concentrationconcentrated under reduced pressure
  15. customto obtain a crystalline product
  16. customThere was obtained 950 mg

出典と根拠

ORDレコード
ord-7f01f9dda47c4d209030b7b666ca05f3
出典データセット
uspto-grants-1988_09
特許番号
US04771008

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