2,2,2-Trifluoroethylamine hydrochloride → HCID 86656357, compound

HRID 1942487Notes

Reaction equation

HRID 1942487 reaction equation
[F:1][CH:2]([F:47])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:22]([N:24]([CH:41]([CH3:43])[CH3:42])[C@H:25]3[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:28]([CH2:38][CH:39]=O)[CH2:27][CH2:26]3)=[O:23])[C:16]([C:18]([F:21])([F:20])[F:19])=[CH:17][C:12]=2[O:11][C:10]([CH3:45])([CH3:44])[C:9]1=[O:46])=[O:4].Cl.[F:49][C:50]([F:54])([F:53])[CH2:51][NH2:52].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)C.C(O)(=O)C>[F:1][CH:2]([F:47])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:22]([N:24]([CH:41]([CH3:43])[CH3:42])[C@H:25]3[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[C@@H:28]([CH2:38][CH2:39][NH:52][CH2:51][C:50]([F:54])([F:53])[F:49])[CH2:27][CH2:26]3)=[O:23])[C:16]([C:18]([F:19])([F:21])[F:20])=[CH:17][C:12]=2[O:11][C:10]([CH3:45])([CH3:44])[C:9]1=[O:46])=[O:4]

Participants

7

Reactant 4

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86656356HCID 86656356, compound

Product 1

HCID 86656357HCID 86656357, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (2R,5R)-5-[{[4-{2-[(difluoroacetyl)amino]ethyl}-2,2-dimethyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]-2-(2-oxoethyl)piperidine-1-carboxylate (377 mg) in ethanol (3 ml) were added 2,2,2-trifluoroethylamine hydrochloride (227 mg), acetic acid (128 μl), sodium triacetoxyborohydride (367 mg), and the mixture was stirred at room temperature for 19 hours. To the reaction solution was added a saturated aqueous sodium hydrogen carbonate solution (2 ml), and the mixture was extracted with ethyl acetate (50 ml). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: chloroform/methanol=99/1) to give the title compound (425 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-f06500a728b9414c95abb94af3ecbe65
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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