Trifluoroacetic acid → HCID 89407631, compound

HRID 526314Notes

Reaction equation

HRID 526314 reaction equation
C(OC([NH:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][F:24])[CH:16]=1)[CH2:10][C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][F:24])[CH:16]=1)[CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 89407762HCID 89407762, compound

Product 1

HCID 89407631HCID 89407631, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 3-[(tert-butoxycarbonyl)amino]-3-[3-(2-fluoroethoxy)phenyl)propanoate (5.0 g, 20 mmol) in dichloromethane was added trifluoro acetic acid (5.64 mL, 73 mmol). After stirring for 24 hours at room temperature additional trifluoro acetic acid (1.13 mL) was added and stirring was continued for 20 hours. The mixture was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (methanol in dichloromethane 0% to 40%)) to yield 4.9 g methyl 3-amino-3-[3-(2-fluoroethoxy)phenyl]propanoate.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by chromatography on silica gel (methanol in dichloromethane 0% to 40%))

Sources & evidence

ORD record
ord-bff1e0e6bf204561861736d0013c8780
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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