Acetaldehyde, 2,2-dimethoxy- → (S)-4-(2,2-Dimethoxy-ethylamino)-3-hydroxy-butyric acid methyl ester

HRID 2095524Notes

Reaction equation

HRID 2095524 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C@H:5]([OH:8])[CH2:6][NH2:7].Cl.COC(=O)C[C@H](O)CN.C(=O)([O-])O.[Na+].[CH3:25][O:26][CH:27]([O:30][CH3:31])[CH:28]=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:9])[CH2:4][C@H:5]([OH:8])[CH2:6][NH:7][CH2:28][CH:27]([O:30][CH3:31])[O:26][CH3:25]

Participants

7

Reactant 4

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 516892Sodium BicarbonateHCID 9898943methyl (3S)-4-amino-3-hydroxybutanoate hydrochloride2×HCID 9898944Methyl (3s)-4-amino-3-hydroxybutanoate

Product 1

HCID 86652695(S)-4-(2,2-Dimethoxy-ethylamino)-3-hydroxy-butyric acid methyl esterYield 116.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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+).

Workup

  1. filtrationAfter filtration
  2. customthe solution was evaporated
  3. dissolutiondissolved in toluene
  4. customevaporated under reduced pressure (2×)

Sources & evidence

ORD record
ord-739e3abc8cd145abb62d84ccca82284e
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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