Trifluoroacetic acid → (2S,3S)-3-methyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2,4-dioxo-1-imidazolidinyl}pentanoic Acid

HRID 1174183Notes

Reaction equation

HRID 1174183 reaction equation
[CH3:1][C@@H:2]([CH2:26][CH3:27])[C@H:3]([N:11]1[CH2:15][C:14](=[O:16])[N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[C:12]1=[O:25])[C:4]([O:6]C(C)(C)C)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C@@H:2]([CH2:26][CH3:27])[C@H:3]([N:11]1[CH2:15][C:14](=[O:16])[N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[C:12]1=[O:25])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68770630HCID 68770630, compound

Product 1

HCID 66889813(2S,3S)-3-methyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2,4-dioxo-1-imidazolidinyl}pentanoic AcidYield 116.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 36D (0.154 g, 0.410 mmol) in dichloromethane (3 mL) was treated with trifluoracetic acid (3 mL), stirred at 25° C. for 16 hours and concentrated. The residue was purified by reversed phase chromatography on a C18 column eluting with a gradient starting with 5-100% acetonitrile in water (0.1% TFA) to give the title compound (0.153 g) as the trifluoroacetic acid salt.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reversed phase chromatography on a C18 column
  3. washeluting with a gradient

Sources & evidence

ORD record
ord-e09747076ff64d0b81e03d922deab7de
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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