Trifluoroacetic acid → (2S)-2-(3-benzyl-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoic acid

HRID 1174300Notes

Reaction equation

HRID 1174300 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]([O:16]C(C)(C)C)=[O:15])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([C:21]([CH3:23])([CH3:22])[CH3:24])[C:14]([OH:16])=[O:15])[C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67405684tert-butyl(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoate

Product 1

HCID 42626247(2S)-2-(3-benzyl-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 111-5 in dichloromethane (1.5 L) was added triflouroacetic acid (810 mL). The mixture was stirred at room temperature for 3 hours and concentrated. The residue was chased with heptanes (4×500 mL). The product was partitioned between dichloromethane (1.5 L) and 5% KH2PO4 (1.1 L). The organic layer was washed with 5% KH2PO4 (900 mL) and brine (900 mL), and concentrated. A solution of the residue in dichloromethane (500 mL) was dried over MgSO4, filtered and concentrated. The residue was recrystallized twice from isopropyl alcohol/water to afford the title compound. 1H NMR (DMSO-d6): δ 7.2-7.4(m, 5H), 4.28(d, 2H), 4.21(s, 1H), 3.47-3.64(m, 2H), 3.08-3.2(m, 2H), 1.0(s, 9H).

Workup

  1. concentrationconcentrated
  2. customThe product was partitioned between dichloromethane (1.5 L) and 5% KH2PO4 (1.1 L)
  3. washThe organic layer was washed with 5% KH2PO4 (900 mL) and brine (900 mL)
  4. concentrationconcentrated
  5. dry with materialA solution of the residue in dichloromethane (500 mL) was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized twice from isopropyl alcohol/water

Sources & evidence

ORD record
ord-0977f4b22d4244ef98751220588fc9e1
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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