Formaldehyde → HCID 117608158, compound

HRID 58830Notes

Reaction equation

HRID 58830 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([CH2:9][C@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:11]([O:13][CH3:14])=[O:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:23]=O>CO.[Pd]>[C:19]([O:18][C:16]([NH:15][C@@H:10]([CH2:9][CH:4]([CH2:3][CH2:2][NH:1][CH3:23])[C:5]([O:7][CH3:8])=[O:6])[C:11]([O:13][CH3:14])=[O:12])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 117608156HCID 117608156, compound

Product 1

HCID 117608158HCID 117608158, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The crude (4S)-dimethyl 2-(2-aminoethyl)-4-((tert-butoxycarbonyl)amino)pentanedioate (5.00 g, 15.7 mmol) was dissolved in methanol (100 mL) and 40% formaldehyde (1.0 g, 14 mmol) and Pd/C (0.8 g) were added. The mixture was stirred under H2 atmosphere (20 psi) for 8 h at ambient temperature. The mixture was filtered through a pad of Celite and the filtrate was evaporated under reduced pressure to afford (2S)-dimethyl 2-((tert-butoxycarbonyl)amino)-4-(2-(methylamino)ethyl)pentane dioate (5.0 g, crude) as a dark brown oil.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-67a8c9c638e541939f140f70c65e6926
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

Loading…