118317-76-3 → Methyl N-(tert-butoxycarbonyl)-3-oxoserinate

HRID 373300Notes

Reaction equation

HRID 373300 reaction equation
[C:1]([NH:8][CH:9]([C:14]([O:16]CC1C=CC=CC=1)=[O:15])[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CO.[Pd]>[C:1]([NH:8][CH:9]([C:14]([OH:16])=[O:15])[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 15018080118317-76-3

Product 1

HCID 11128196Methyl N-(tert-butoxycarbonyl)-3-oxoserinateYield 107%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

BOC-NHCH(CO2Me)CO2CH2Ph (16.2 g) was dissolved in MeOH (250 ml), to which was added 20% Pd/C (0.66 g). The suspension was purged with H2 for 1.5 hours, filtered, and stripped at 30° in vacuo, giving a syrup (12.5 g) which was kept at 4° until use in the following step.

Workup

  1. customThe suspension was purged with H2 for 1.5 hours
  2. filtrationfiltered
  3. customstripped at 30° in vacuo

Sources & evidence

ORD record
ord-c816aecf14c64b5b84dce79ba1583765
Source dataset
uspto-grants-1992_11
Patent number
US05162527

Reaction notes

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