Trifluoroacetic acid → HCID 53713896, compound

HRID 273869Notes

Reaction equation

HRID 273869 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH2:25][C@H:26]([N:28]([CH2:36][CH2:37][O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[O:45][CH2:46][C:47]([F:50])([F:49])[F:48])C(OC(C)(C)C)=O)[CH3:27])=[CH:19][C:20]=2[C:22]([NH2:24])=[O:23])[CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH2:25][C@H:26]([NH:28][CH2:36][CH2:37][O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[O:45][CH2:46][C:47]([F:50])([F:49])[F:48])[CH3:27])=[CH:19][C:20]=2[C:22]([NH2:24])=[O:23])[CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 53774142HCID 53774142, compound

Product 1

HCID 53713896HCID 53713896, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(-)-1-(4-benzyloxybutyl)-5-[2-[N-tert-butoxycarbonyl-2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carboxamide (523 mg) in methylene chloride (7.5 ml) was added dropwise trifluoroacetic acid (1.5 ml) with stirring under ice cooling, and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added a saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of chloroform and methanol (10/1) as eluent to give 388 mg of (R)-(-)-1-(4-benzyloxybutyl)-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carboxamide melting at 101°-102° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  6. additiona mixture of chloroform and methanol (10/1) as eluent

Sources & evidence

ORD record
ord-6fc42638b9a94356afe2ce93766013f4
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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