HCID 18631486, compound → HCID 15104726, compound

HRID 1194992Notes

Reaction equation

HRID 1194992 reaction equation
C(OC([NH:11][C:12](=[O:22])[C@@H:13]([C@H:15]([CH3:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH2:14])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:17]([O:16][C@@H:15]([CH3:21])[C@H:13]([C:12]([NH2:11])=[O:22])[NH2:14])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 18631486HCID 18631486, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15104726HCID 15104726, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (1.5 g) is added to a solution of the compound obtained in step (a) in MeOH (200 ml), and hydrogen is bubbled through the reaction mixture for 1.5 h, checking the disappearance of the starting compound by tlc. When the reaction is over, excess hydrogen is removed by passing a nitrogen stream through the mixture, the reaction mixture is filtered over celite and the filtrate is concentrated to dryness thus yielding O-tert-butyl-D-threonineamide (2.55 g, 99%). Both mass and NMR spectra confirm the assigned structure.

Workup

  1. customis bubbled through the reaction mixture for 1.5 h
  2. customis removed
  3. filtrationthe reaction mixture is filtered over celite
  4. concentrationthe filtrate is concentrated to dryness thus yielding O-tert-butyl-D-threonineamide (2.55 g, 99%)

Sources & evidence

ORD record
ord-98e76244533e460ba354fb424d06b291
Source dataset
uspto-grants-1989_03
Patent number
US04816560

Reaction notes

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