Boc-Asn-Leu-Gly-OBzl → HCID 131718986, compound

HRID 35816Notes

Reaction equation

HRID 35816 reaction equation
[NH:1]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([O:21]CC1C=CC=CC=1)=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[H][H]>C(O)C.[Pd]>[NH:1]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

5

Reactant 2

HCID 13470952Boc-Asn-Leu-Gly-OBzlHCID 178418361HCID 178418361, compound

Product 1

HCID 131718986HCID 131718986, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The crude Boc-Asn-Leu-Gly-OBzl was suspended in 2.0 l 50% ethanol. Addition of 10 g 10% Palladium on carbon and hydrogenation for one hour at 3 bar hydrogen pressure under stirring. The crude solution was filtrated and pH adjusted to 3.0 with a 1N sodium hydrochloric acid solution. Removal of ethanol under vacuum at 40° C. resulted in crystallisation of product. Filtration and drying under vacuum at 40° C. for 2 days gave the pure product. Yield 72.3 g (58%).

Workup

  1. filtrationThe crude solution was filtrated
  2. customRemoval of ethanol under vacuum at 40° C.
  3. customresulted in crystallisation of product
  4. filtrationFiltration
  5. customdrying under vacuum at 40° C. for 2 days
  6. customgave the pure product

Sources & evidence

ORD record
ord-4018d13b4d6642c38ed3d27f679dec25
Source dataset
uspto-grants-1995_05
Patent number
US05411942

Reaction notes

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