Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | (3S)-2,5-dioxooxolan-3-yl acetate | HCID 11126528 | — |
| Reactant | 3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine | HCID 57403052 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | HCID 67111545 | HCID 67111545 | — |
Reaction Steps
To 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine (70 mg, 0.194 mmol) and (S)-(−)-2-acetoxysuccinic anhydride (34 mg, 213 μmol) was added benzene (1.9 mL) and acetic acid (55 μl, 0.968 mmol) before it was stirred at 80° C. for 1 h. The reaction mixture was concentrated before the regioisomers were separated via SFC (Column: Chiralpak IC, Mobile Phase: liquid CO2/40% MeOH) to give (2S)-2-acetoxy-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoic acid. MS (ESI) m/z: Calculated: 519.1; Observed: 520.1 (M++H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07842685B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-5de795aa9e4a4677abbd83b23bcbfcb8 |
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| Source note | uspto-grants-2010_11 |
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