Methylamine → (3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide

HRID 440115노트

반응식

HRID 440115 반응식
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:17][C@H:16]2[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][NH2:19]>C(O)C>[NH2:19][C@@H:18]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@H:6]([OH:7])[CH2:8][N:9]1[C@H:8]([C:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:17][C@H:16]2[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10]1

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 454736(3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamide

생성물 1

HCID 9865804(3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

(A)(ii) A suspension of 26.55 g of N-tert.butyl-2-[2(R)-hydroxy-4-phenyl-3(S)-phthalimidobutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide (prepared as described in Example 1) in 100 ml of ethanol was treated with 25 ml of a 30% solution of methylamine in ethanol at room temperature for 1 hour. The mixture was evaporated to dryness under reduced pressure. The residue was dissolved in 250 ml of ethanol, treated with 250 ml of a saturated solution of hydrogen chloride in ethyl acetate and stirred at room temperature for 16 hours. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The aqueous phase was separated, made basic with solid sodium carbonate and then extracted with dichloromethane. The dichloromethane extract was washed with sodium chloride solution and evaporated to dryness. The residue was triturated with diethyl ether and, after filtration, there were obtained 17.48 g of 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide as a white solid; MS: m/e 402 [M+H]+.

후처리

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in 250 ml of ethanol
  3. additiontreated with 250 ml of a saturated solution of hydrogen chloride in ethyl acetate
  4. customThe mixture was evaporated to dryness
  5. customthe residue was partitioned between ethyl acetate and water
  6. customThe aqueous phase was separated
  7. extractionextracted with dichloromethane
  8. extractionThe dichloromethane extract
  9. washwas washed with sodium chloride solution
  10. customevaporated to dryness
  11. customThe residue was triturated with diethyl ether
  12. filtrationafter filtration

출처 및 근거

ORD 기록
ord-fbe68dcdc64e4e1b80204200ba95c47e
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516913

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