HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Octanediol → (R)-3-[8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Octanediol | HCID 69420 | — |
| Reactant | 4-(Bromomethyl)-2-fluoro-1-(trifluoromethyl)benzene | HCID 2737574 | — |
| Reactant | (R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride | HCID 46223507 | — |
| Reactant | 8-(3-Fluoro-4-trifluoromethyl-benzyloxy)-octan-1-ol | HCID 66875062 | — |
| Reactant | 8-(3-Fluoro-4-trifluoromethyl-benzyloxy)-octanoic acid | HCID 66875129 | — |
| Product | (R)-3-[8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester | HCID 66875228 | — |
Reaction Steps
The title compound, m/e=463.5 ([M−H]−), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 3-fluoro-4-trifluoromethyl-benzyl bromide, leading to 8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-[8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08349893B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-9c41cedd2a5348fe9f5273636f38c95b |
| Source note | uspto-grants-2013_01 |