HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (S)-mandelic acid | HCID 439616 | — |
| Reactant | (S)-2-Amino-5-(3-pyridyl)pentane | HCID 13739742 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide | HCID 13999762 | — |
Reaction Steps
Under the conditions outlined in Example 14a, 76.2 g of the amine was reacted with 74.2 g of (S)-mandelic acid in the presence of 105.2 g of 1,3-dicyclohexylcarbodiimide and 78.4 g of 1-hydroxybenzotriazole in 1L of dimethylformamide. A similar workup furnished 109 g of [S-(S*,S*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide, mp 143°-145° C., [α]D25 +27.8° (c, 1.0, MeOH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04975438 |
| Source dataset | uspto-grants-1990_12 |
| ORD ID | ord-913fb522c36f41f1b49859dbaa9e09ae |
| Source note | uspto-grants-1990_12 |