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

HRID 2224027ノート

反応式

HRID 2224027 の反応式
[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]

参加物

5

反応物 3

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

生成物 2

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

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-1b8ff0baf7bf4ead854647f6b1f9670e
出典データセット
uspto-grants-2008_05
特許番号
US07378410B2

反応ノート

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