Dichloromethane → (3S,6R)-3-amino-6-(6-azido-hexyloxy)-1-methyl-azepan-2-one

HRID 2224027노트

반응식

HRID 2224027 반응식
[C:1]([O:5]C(=O)[NH:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]=[N+:23]=[N-:24])[CH2:11][N:10]([CH3:25])[C:9]1=[O:26])(C)(C)C.C(O)(C(F)(F)F)=O.[CH2:35]([Cl:37])[Cl:36]>>[CH3:1][OH:5].[CH2:35]([Cl:37])[Cl:36].[NH3:7].[NH2:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]=[N+:23]=[N-:24])[CH2:11][N:10]([CH3:25])[C:9]1=[O:26]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86609579[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester

생성물 2

HCID 21584172Ammonia methanol dichloromethane수율 10%HCID 86609578(3S,6R)-3-amino-6-(6-azido-hexyloxy)-1-methyl-azepan-2-one수율 88%

실험 절차

To a stirred solution of [(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.32 g, 0.83 mmol) in CH2Cl2 (4 mL) is added TFA (1 mL) at room temperature. After 1 h, the reaction is evaporated under vacuum, toluene (20 mL) is added and evaporated under vacuum to remove remaining TFA. The residue is dissolved in CH2Cl2 (20 mL) saturated with NH3 adsorbed on silica and chromatographed (50% EtOAc/CH2Cl2/NH3 then 10% CH3OH/CH2Cl2/NH3) to give 0.207 g (88%) of (3S,6R)-3-amino-6-(6-azido-hexyloxy)-1-methyl-azepan-2-one as an oil. MS (ESI) 284.2 (M+H)+

후처리

  1. customthe reaction is evaporated under vacuum, toluene (20 mL)
  2. additionis added
  3. customevaporated under vacuum
  4. customto remove
  5. dissolutionThe residue is dissolved in CH2Cl2 (20 mL) saturated with NH3
  6. customchromatographed (50% EtOAc/CH2Cl2/NH3

출처 및 근거

ORD 기록
ord-1b8ff0baf7bf4ead854647f6b1f9670e
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378410B2

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