Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Dichloromethane methanol | HCID 21226129 | — |
| Reactant | HCID 68765681 | HCID 68765681 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68767051 | HCID 68767051 | — |
Reaction Steps
A suspension of (R)-2-Amino-4-(3-hexanoylamino-4-hydroxy-phenyl)-2-methyl-butyric acid methyl ester trifluoro acetic acid salt (460 mg, 1.02 mmol) in dry toluene was heated under pressure (microwave Emrys optimizer) to 200° C. for 10 minutes. After cooling to RT the reaction mixture was distributed between AcOEt and a saturated aqueous NaHCO3 solution. Silica gel chromatography (eluent CH2Cl2/MeOH 10/1) provided the title compound as an amorphous colorless solid. 1H-NMR (DMSO-d6): 7.51 (d, J=8.3 Hz; 1H), 7.42 (d, J=1.2 Hz; 1H), 7.12 (dd, J=8.3, 1.2 Hz; 1H), 3.60 (s; 3H), 2.88 (t, J=7.4 Hz; 2H), 2.71-2.63/2.58-2.50 (m; 2H), 1.92 (bs; 2H), 1.90-1.82/1.80-1.73 (m; 2H), 1.43-1.28 (m; 4H), 1.22 (s; 3H), 0.85 (m; 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07825260B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-887dd4f6c4e24ce4958a6d02cce68464 |
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| Source note | uspto-grants-2010_11 |
|---|