Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | Ethyl Indoline-2-carboxylate | HCID 11949691 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 68281671 | HCID 68281671 | — |
Reaction Steps
16.6 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and then 10 g of ethyl indoline-2-carboxylate are added to a solution of 12.6 g of o-benzyl-D-lactic acid in 30 ml of DMF and 10.6 ml of pyridine. The reaction medium is stirred at ambient temperature for 18 hours. The reaction medium is concentrated under reduced pressure to ⅔ of the volume of the reaction medium. Ethyl acetate and water are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica cartridge: eluent: gradient: heptane/ethyl acetate from 100/0 to 80/20, so as to give 7.24 g of 1-((R)-2-benzyloxypropionyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester: diastereoisomer A, the characteristics of which are the following:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09133168B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-81c374e5b6a94791aaa75a0f2fbc2d74 |
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| Source note | uspto-grants-2015_09 |
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