Methyl (4R)-1,3,4,5,6,7,8,9,10,12-decahydro-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylate → HCID 54075283、化合物

HRID 234218ノート

反応式

HRID 234218 の反応式
C[O:2][C:3]([C@H:5]1[NH:18][C:17](=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:20])[C:10]2[C:21]([CH3:28])=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([OH:25])[C:9]=2[CH2:8][S:7][CH2:6]1)=O>CO.C(N)C#C>[CH2:17]([NH:18][C:3]([C@H:5]1[NH:18][C:17](=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:20])[C:10]2[C:21]([CH3:28])=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([OH:25])[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:2])[C:16]#[CH:15]

参加物

4

反応物 1

HCID 9823853Methyl (4R)-1,3,4,5,6,7,8,9,10,12-decahydro-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylate

生成物 1

HCID 54075283HCID 54075283、化合物収率 97.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 239041Propargylamine溶媒

反応条件

温度
50 °C

実験手順

A solution of 43 mg of the product of Example 23 in a mixture of 0.5 ml of methanol and 0.5 ml of prop-2-ynylamine was heated to 50° C. for 8 h. The solution was evaporated in vacuo, the residue was dissolved in ethyl acetate, and the solution was washed with 1N hydrochloric acid and water. The organic layer was dried over sodium sulfate and evaporated in vacuo and the residue was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent. The purified product was crystallized from ethyl acetate/hexane to afford 22 mg (R)-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5benzoxathiaazacyclotetradecine-4-carboxylic acid prop-2-ynylamide as a white solid.

後処理

  1. customThe solution was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was washed with 1N hydrochloric acid and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customthe residue was chromatographed on silica gel
  7. customThe purified product was crystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-b4be61aeae4b4dbfadd914aff69d5764
出典データセット
uspto-grants-1997_01
特許番号
US05594135

反応ノート

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