N-(t-Butoxycarbonyl)-alpha-(4-hydroxy-2,3,5,6-tetrahydro-4-pyranyl)glycine, benzyl ester → HCID 13754450, compound

HRID 2118844Notes

Reaction equation

HRID 2118844 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1([OH:26])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:10]([O:12]CC1C=CC=CC=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1([OH:26])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 13754449N-(t-Butoxycarbonyl)-alpha-(4-hydroxy-2,3,5,6-tetrahydro-4-pyranyl)glycine, benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 13754450HCID 13754450, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(t-Butoxycarbonyl)-α-(4-hydroxy-2,3,5,6-tetrahydro-4-pyranyl)glycine, benzyl ester (10.34 g, 28.3 mmoles) and 10% palladium on charcoal (2.0 g) in 200 ml of absolute ethanol was treated with hydrogen at 1 atmosphere for 2 hours. The catalyst was filtered and the solvent removed in vacuo finally by co-evaporation with benzene. A small amount of ethyl acetate induced crystallization. The slurry was triturated with isopropyl ether, filtered and washed with isopropyl ether and hexane and dried in air to give 6.84 g of product as a white solid, melting point 140°-141° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent removed in vacuo finally by co-evaporation with benzene
  3. customcrystallization
  4. customThe slurry was triturated with isopropyl ether
  5. filtrationfiltered
  6. washwashed with isopropyl ether and hexane
  7. customdried in air

Sources & evidence

ORD record
ord-b7ef747e5fd24519a4a1d3b14d52a47a
Source dataset
uspto-grants-1987_07
Patent number
US04680388

Reaction notes

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