GlcA Ile-Phe-OBzl → GlcA Ile-Phe-OH

HRID 256463Notes

Reaction equation

HRID 256463 reaction equation
[OH:1][CH:2]1[O:10][C@H:9]([C:11](=[O:13])[OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[NH2:14][C@H:15]([C:20]([NH:22][C@H:23]([C:31]([O:33]CC1C=CC=CC=1)=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17]>CN(C=O)C.O.[Pd]>[OH:1][CH:2]1[O:10][C@H:9]([C:11](=[O:12])[OH:13])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[NH2:14][C@H:15]([C:20]([NH:22][C@H:23]([C:31]([OH:33])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17]

Participants

4

Reactant 1

HCID 131715369GlcA Ile-Phe-OBzl

Product 1

HCID 131715371GlcA Ile-Phe-OHYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

GlcA-Ile-Phe-OBzl (1.04 g, 1.9 mmol) was hydrogenolyzed in presence of palladium/activated charcoal (10% Pd) (200 mg) in DMF-water (9:1, v/v) solution for 5 h. After removal of the catalyst by filtration the solution was evaporated to dryness and the product was recovered by lyophilization from water with 98% yield (0.85 g); mp 173°-174° C.; [α]54625 =+3,36 (c=1, MeOH); Rf(A) =0.15.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration the solution
  3. customwas evaporated to dryness
  4. customthe product was recovered by lyophilization from water with 98% yield (0.85 g)

Sources & evidence

ORD record
ord-51a87225c38a411787f5b791d2b1e93f
Source dataset
uspto-grants-1987_10
Patent number
US04703107

Reaction notes

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