HuagongsheHuagongshe Chemistry Print Report · For research reference only
(3aR*,10aS*)-9-[4-(benzyloxycarbonylamino)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one → (3aR*,10aS*)-9-(4-Aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-one hydrobromide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (3aR*,10aS*)-9-[4-(benzyloxycarbonylamino)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one | HCID 15385743 | — |
| Reactant | Acetic Acid Mixture with Hydrobromic Acid | HCID 21893785 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | (3aR*,10aS*)-9-(4-Aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-one hydrobromide | HCID 67767990 | 92% |
Reaction Steps
To a solution of (3aR*,10aS*)-9-[4-(benzyloxycarbonylamino)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (366 mg, 0.58 mmol) in chloroform (3 mL) was added 25% hydrogen bromide/acetic acid (1 mL) and the mixture was stirred at room temperature for 75 minutes. This reaction mixture was concentrated under reduced pressure and the residue was crystallized from ethanoldiethyl ether to provide 309 mg (yield 92%) of the title compound. m.p. 222°-224° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05866567 |
| Source dataset | uspto-grants-1999_02 |
| ORD ID | ord-dc7cda3d08c24748a8e184060a5055c6 |
| Source note | uspto-grants-1999_02 |