Trifluoromethanesulfonic acid → HCID 68441581, compound

HRID 2246906Notes

Reaction equation

HRID 2246906 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:9]([OH:20])[CH2:8][N:7]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:5])[CH3:2].[CH3:29][O:30][CH2:31][CH2:32][CH2:33][N:34]1[C:39]2[CH:40]=[C:41]([CH2:44]OC(=N)C(Cl)(Cl)Cl)[CH:42]=[CH:43][C:38]=2[O:37][CH2:36][C:35]1=[O:52].FC(F)(F)S(O)(=O)=O>ClCCl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:9]([O:20][CH2:44][C:41]2[CH:42]=[CH:43][C:38]3[O:37][CH2:36][C:35](=[O:52])[N:34]([CH2:33][CH2:32][CH2:31][O:30][CH3:29])[C:39]=3[CH:40]=2)[CH2:8][N:7]1[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 68439676HCID 68439676, compoundHCID 68440355HCID 68440355, compound

Product 1

HCID 68441581HCID 68441581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5.20 g of (2S,4R,5R)-5-hydroxy-1,4-bis(4-methoxy-phenyl)piperidine-2-carboxylic acid ethyl ester and 5.62 g of 2,2,2-trichloro-acetimidic acid 4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl ester in 150 ml of dichloromethane is added 1.1 ml of trifluoromethanesulfonic acid at −0° C. The reaction mixture is allowed to stir for another hour at this temperature and then allowed to warm to 0° C. within 2 hours. The mixture is quenched by addition of 2N sodium hydroxide, extracted with dichlormethane, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a brown oil. Rf=0.15 (EtOAc-heptane 1:1); Rt=4.73.

Workup

  1. customThe mixture is quenched by addition of 2N sodium hydroxide
  2. extractionextracted with dichlormethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-5381fac6f3604d329dc1eced894a4627
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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