HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl 4-carboxyphenylacetate → Pivalic acid (R)-6-{2-[(4-carboxymethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl 4-carboxyphenylacetate | HCID 19966080 | — |
| Reactant | HCID 57934485 | HCID 57934485 | — |
| Reactant | pivalic acid (R)-6-{2-[(4-benzyloxycarbonylmethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester | HCID 86605269 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Pivalic acid (R)-6-{2-[(4-carboxymethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester | HCID 86605268 | 97.7% |
Reaction Steps
From pivalic acid (R)-6-[2-(ethoxycarbonylmethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-yl ester (150 mg) and 4-benzyloxycarbonylmethylbenzoic acid (138 mg), according to an analogous synthetic method to Preparation Example 154, obtained was pivalic acid (R)-6-{2-[(4-benzyloxycarbonylmethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (200 mg). A solution thereof in methanol (5 ml) was subjected to a catalytic reduction in the presence of 10% palladium-activated charcoal (40 mg) for 2 hours at room temperature under hydrogen atmosphere at ambient pressure. After filtration through celite pad, the solution was concentrated in vacuo to provide the title compound (170 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399520B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-f6f639ce7978458ca04303dc776165f8 |
| Source note | uspto-grants-2013_03 |