Trifluoroacetic acid → HCID 58497698, compound

HRID 1519214Notes

Reaction equation

HRID 1519214 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:16][O:17][C:18]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][C:21]2[CH2:22][C@@H:23]3[C@H:28]([CH3:29])[C@:27]([CH3:30])([C:20]=2[C:19]=1[N+:36]([O-:38])=[O:37])[CH2:26][CH2:25][NH:24]3.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.C(N(CC)CC)C>[CH:1]1([C:6]([N:24]2[CH2:25][CH2:26][C@:27]3([CH3:30])[C@@H:28]([CH3:29])[C@H:23]2[CH2:22][C:21]2[CH:31]=[C:32]([N+:33]([O-:35])=[O:34])[C:18]([O:17][CH3:16])=[C:19]([N+:36]([O-:38])=[O:37])[C:20]=23)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 78284Cyclopentanecarbonyl chlorideHCID 58497625HCID 58497625, compound

Product 1

HCID 58497698HCID 58497698, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Cyclopentanecarbonyl chloride (0.12 g) is added to the trifluoroacetic acid salt of (2R,6R,11R)-8-methoxy-6,11-dimethyl-7,9-dinitro-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine (0.43 g) and triethylamine (0.31 mL) dissolved in dichloromethane (10 mL). The resulting solution is stirred at room temperature overnight. Then, aqueous Na2CO3 solution is added and the resulting mixture is extracted with dichloromethane. The combined extracts are washed with water and dried (Na2SO4) and the solvent is evaporated. The residue is purified by HPLC on reversed phase (MeCN/H2O) to give the product as a white solid.

Workup

  1. extractionthe resulting mixture is extracted with dichloromethane
  2. washThe combined extracts are washed with water
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe residue is purified by HPLC on reversed phase (MeCN/H2O)

Sources & evidence

ORD record
ord-6e9f96fa63d24811b12a487ef944f887
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

Loading…