Trifluoroacetic acid → Ethyl 2-(6-aminochroman-2-yl)acetate
Reaction equation
C1(C)C=CC=CC=1.C(OC([NH:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][CH:21]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20][CH2:19]2)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[NH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][CH:21]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20][CH2:19]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Into the ethyl 2-(6-(tert-butyloxycarbonylamino)chroman-2-yl)acetate toluene solution of Example 3 (7 L) was added 1480 g of trifluoroacetic acid. The solution was warmed to 60° C. for 2 h. After distilling-off about 2 L of toluene under reduced pressure (T≦60° C.), the mixture was cooled to room temperature. About 10 L of 10% (w/w) of aqueous sodium bicarbonate was added slowly to the well-stirred mixture until the pH was above 7. The mixture was stirred for 20 min and the aqueous fraction separated. The aqueous fraction was extracted with 3×1 L of toluene. The combined organic fractions were washed with 3 L of brine, dried over 200 g of anhydrous sodium sulfate, and filtered. The volume of solvent was reduced to 6 L by distillation under reduced pressure (T≦60° C.) to provide a toluene solution of ethyl 2-(6-aminochroman-2-yl)acetate.
Workup
- customthe aqueous fraction separated
- extractionThe aqueous fraction was extracted with 3×1 L of toluene
- washThe combined organic fractions were washed with 3 L of brine
- dry with materialdried over 200 g of anhydrous sodium sulfate
- filtrationfiltered
- distillationThe volume of solvent was reduced to 6 L by distillation under reduced pressure (T≦60° C.)
Sources & evidence
- ORD record
- ord-ed8e18ef06da4d609411b0f51f61eba2
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06903227B2
Reaction notes
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