Hydrochloric Acid → HCID 53793219, compound

HRID 1375038Notes

Reaction equation

HRID 1375038 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:44])[C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=2)[C@H:25]([CH2:45][C:46]2[CH:51]=[CH:50][C:49](O)=[C:48]([O:53][CH3:54])[CH:47]=2)[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C(C)=CC=CC=1C.Cl>CN(C)C1C=CN=CC=1.ClCCl.O>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:35]=[C:30]([CH:31]=[C:32]([C:40]([F:41])([F:42])[F:43])[CH:33]=1)[C:29]([N:26]1[CH2:27][CH2:28][N:23]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][C@H:25]1[CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[C:48]([O:53][CH3:54])[CH:47]=1)=[O:44]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 54006018HCID 54006018, compound

Product 1

HCID 53793219HCID 53793219, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoromethane sulfonic acid anhydride (5.25 ml) was added dropwise over 30 minutes to an ice-cooled solution of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-hydroxy-3-methoxybenzyl)piperazine (14.3 g) and 4-(dimethylamino)pyridine (0.47 g) and 2,6-lutidine (3.6 ml) in dichloromethane (150 ml) below 10° C. After being stirred at the same temperature for 2 hours, the reaction mixture was poured into water. The pH of the whole mixture was adjusted to 7 with diluted hydrochloric acid and the organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of toluene and ethyl acetate (100:1–5:1) to give the objective trifluoromethanesulfonic acid 4-[[(2R)-1-[3,5-bis(trifluoro-methyl)benzoyl]-4-benzylpiperazin-2-yl]methyl]-2-methoxyphenyl ester as an oil.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of toluene and ethyl acetate (100:1–5:1)

Sources & evidence

ORD record
ord-7c1b0d0be0594bcd94581bdde3b32ec3
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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