Formaldehyde → HCID 18418729, compound

HRID 990390Notes

Reaction equation

HRID 990390 reaction equation
[CH:1]([NH:4][C@@H:5]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([OH:8])=[O:7])([CH3:3])[CH3:2].[CH2:13]=O.[H][H]>C(O)C.[Pd]>[CH:1]([N:4]([CH3:13])[CH:5]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([OH:8])=[O:7])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 15852242HCID 15852242, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18418729HCID 18418729, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-2-isopropylamino-4-methyl-pentanoic acid (70.86 g, 0.41 mol, Example 19, Step A) and aqueous HCHO (94 mL of 37.2%) was agitated in an atmosphere of hydrogen (pressure, 47-52 psi) at 50° C. in absolute ethanol (1.5 L) in the presence of Pd/C (20%, 5 g) until the absorption of hydrogen almost ceased. The catalyst was removed by filtration. The filtrate was concentrated in vacuo to dryness. One hundred milliliters of water was added and concentrated to dryness, and this operation was repeated twice to remove most of HCHO. Absolute ethanol (100 mL) was then added and concentrated to dryness to remove residual water. The white solid collected was triturated with acetone. Filtration and drying under vacuum gave 69.39 g (89%) of the desired product as a white solid; mp 159-160° C. APCI-MS m/z 188.2 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo to dryness
  3. additionOne hundred milliliters of water was added
  4. concentrationconcentrated to dryness
  5. customto remove most of HCHO
  6. additionAbsolute ethanol (100 mL) was then added
  7. concentrationconcentrated to dryness
  8. customto remove residual water
  9. customThe white solid collected
  10. customwas triturated with acetone
  11. filtrationFiltration
  12. customdrying under vacuum

Sources & evidence

ORD record
ord-0612bf01269340d5967cd3208557776b
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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