HuagongsheHuagongshe Chemistry Print Report · For research reference only
Homoallyl bromide → (2R,3S) N1-[(3S)-1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-(3-buten-1-yl)-butanediamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Homoallyl bromide | HCID 21241 | — |
| Reactant | Succinate | HCID 160419 | — |
| Reactant | 3-Amino-1-methyl-5-phenyl-1H-benzo[E][1,4]diazepin-2(3H)-one | HCID 2729681 | — |
| Reactant | (2R,3S)N1-[1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-allyl-N4-[3,5-difluorobenzyl]-butanediamide | HCID 9916426 | — |
| Product | (2R,3S) N1-[(3S)-1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-(3-buten-1-yl)-butanediamide | HCID 9912782 | — |
Reaction Steps
A procedure analogous to the preparation of Example 5 was followed. The appropriate succinate ester was prepared using the method disclosed in PCT publication WO 98/51665), using 3-butenyl bromide for R3—X in place allyl bromide (see Scheme 2). The anti-succinate half-ester was coupled to (S)-isomer benzodiazepine (30) using the procedures of Step 1. After Steps 2 and 3, the title compound was isolated. MS (M+H)+=475.3; (M+Na)+=497.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07456172B2 |
| Source dataset | uspto-grants-2008_11 |
| ORD ID | ord-3fc39e7433a24db287670b7b6d2de22a |
| Source note | uspto-grants-2008_11 |