HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetaldehyde, 2,2-dimethoxy- → (S)-4-(2,2-Dimethoxy-ethylamino)-3-hydroxy-butyric acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetaldehyde, 2,2-dimethoxy- | HCID 162650 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | methyl (3S)-4-amino-3-hydroxybutanoate hydrochloride | HCID 9898943 | — |
| Reactant | Methyl (3s)-4-amino-3-hydroxybutanoate | HCID 9898944 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (S)-4-(2,2-Dimethoxy-ethylamino)-3-hydroxy-butyric acid methyl ester | HCID 86652695 | 116.3% |
Reaction Steps
A solution of 2.50 g (14.7 mmol) of (S)-4-amino-3-hydroxy-butyric acid methyl ester; HCl (intermediate 24) in 18 ml of methanol was treated with 6.19 g (73.7 mmol) of natriumhydrogencarbonat, 2.2 ml (14.7 mmol) of dimethoxyacetaldehyde (in H2O 60%), 0.250 g of Pd/C (10%) and was stirred over H2-atmosphere for 4 h. After filtration, the solution was evaporated, dissolved in toluene, evaporated under reduced pressure (2×) to yield 3.781 g (70%) of the titled compound as yellow oil. MS: 222.13 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08445674B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-739e3abc8cd145abb62d84ccca82284e |
| Source note | uspto-grants-2013_05 |