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

HRID 2224027Notes

Reaction equation

HRID 2224027 reaction equation
[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]

Participants

5

Reactant 3

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

Product 2

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

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-1b8ff0baf7bf4ead854647f6b1f9670e
Source dataset
uspto-grants-2008_05
Patent number
US07378410B2

Reaction notes

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