HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → Pivalic acid 6-{2-{[4-(2-amino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Pivalic acid 6-{2-{[4-(2-tert-butoxycarbonylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester | HCID 66627582 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Pivalic acid 6-{2-{[4-(2-amino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester | HCID 66627097 | 94.3% |
Reaction Steps
To a solution of pivalic acid 6-{2-{[4-(2-tert-butoxycarbonylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (90 mg) in dichloromethane (1.5 ml) was added trifluoroacetic acid (0.2 ml), and the solution was stirred for 1.5 hours at room temperature. The solution was neutralized by sequentially adding tetrahydrofuran and aqueous ammonia, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (72 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399520B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-5dbdbdf5d8194ffba1180bc4789adda2 |
| Source note | uspto-grants-2013_03 |