HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrogen Bromide → methyl 2-((S)-1-amino-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate hydrobromide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | methyl 2-((S)-1-(benzyloxycarbonylamino)-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate | HCID 59595035 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | methyl 2-((S)-1-amino-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate hydrobromide | HCID 66889567 | 153.1% |
Reaction Steps
To 33% HBr in acetic acid (1.33 L) was added the title compound of Example 5 (403.4 g, 766 mmol) and the stirred vigorously for 1 hour and 20 min. The mixture was slowly and carefully added to MTBE (12 L) with external cooling and strong agitation. The mixture was stirred for 1 hour at 0° C. and filtered under N2. The hygroscopic solids were washed with MTBE (1 L) and dried to constant mass in a vacuum oven to yield the title compound (277.5 g, 76.5%) as a fine brown solid. 1H NMR (CDCl3): consistent with proposed structure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07538129B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-01f361cb86be4320a5eae1291c8048e8 |
| Source note | uspto-grants-2009_05 |