Trifluoroacetic acid → (3R,5S)-5-((S)-1-Amino-2-phenylethyl)-3-methyldihydrofuran-2-one

HRID 1612459Notes

Reaction equation

HRID 1612459 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH:16]1[CH2:20][CH:19]([CH3:21])[C:18](=[O:22])[O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@H:8]([C@H:16]1[O:17][C:18](=[O:22])[C@H:19]([CH3:21])[CH2:20]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57181317[(S)-1-(4-Methyl-5-oxo-tetrahydrofuran-2-yl)-2-phenylethyl]carbamic acid t-butyl ester

Product 1

HCID 68679802(3R,5S)-5-((S)-1-Amino-2-phenylethyl)-3-methyldihydrofuran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(S)-1-(4-methyl-5-oxo-tetrahydrofuran-2-yl)-2-phenylethyl]-carbamic acid t-butyl ester (synthesis described in Journal of Organic Chemistry (1986) 51(21), 3921) (2 g, 6.27 mmol) in DCM (40 ml) was treated with trifluoroacetic acid (5 ml) for 2 h. The solvent was evaporated under reduced pressure, the residue dissolved in DCM, washed with aqueous sodium bicarbonate and dried (Na2SO4). The solvent was evaporated to afford the title compound (D48) as a pale yellow solid (1.25 g)

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in DCM
  3. washwashed with aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-003e79046c824b90bdeec62deccfb6eb
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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