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, 화합물

HRID 234218노트

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HRID 234218 반응식
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]

참가 물질

4

반응물 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

생성물 1

HCID 54075283HCID 54075283, 화합물수율 97.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 239041Propargylamine용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b4be61aeae4b4dbfadd914aff69d5764
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594135

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