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

HRID 1174212Notes

Reaction equation

HRID 1174212 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[N:9]=[C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[S:11][CH:12]=2)[C:5](=[O:19])[CH2:4][N:3]1[C@@H:20]([C@@H:28]([CH3:31])[CH2:29][CH3:30])[C:21]([O:23]C(C)(C)C)=[O:22].FC(F)(F)C(O)=O>ClCCl>[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[N:9]=[C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[S:11][CH:12]=2)[C:5](=[O:19])[CH2:4][N:3]1[C@@H:20]([C@@H:28]([CH3:31])[CH2:29][CH3:30])[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67406421tert-butyl(2S,3S)-2-(2,4-dioxo-3-{[2-(3-pyridinyl)-1,3-thiazol-4-yl]methyl}-1-imidazolidinyl)-3-methylpentanoate

Product 1

HCID 67408846(2S,3S)-2-(2,4-dioxo-3-{[2-(3-pyridinyl)-1,3-thiazol-4-yl]methyl}-1-imidazolidinyl)-3-methylpentanoic AcidYield 153.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 57B (0.090 g, 0.220 mmol) in dichloromethane (2 mL) was treated with trifluoracetic acid (2 mL), stirred at 25° C. for 16 hours, and concentrated. The residue was purified by reversed phase chromatography on a C18 column eluting with 5-100% acetonitrile in water (0.1% TFA) to give the title compound (0.131 g, 90% yield) as the trifluoroacetic acid salt.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reversed phase chromatography on a C18 column
  3. washeluting with 5-100% acetonitrile in water (0.1% TFA)

Sources & evidence

ORD record
ord-e75fd3be7cbc4d5293e3c3f7b2d277ae
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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