HCID 86638446, compound → HCID 24851758, compound

HRID 1009884Notes

Reaction equation

HRID 1009884 reaction equation
[NH2:1][C:2](=[O:73])[C:3]([NH:6][C:7](=[O:72])[CH2:8]/[CH:9]=[CH:10]/[C:11]1[CH:71]=[CH:70][C:14]([CH2:15][C:16]2[C:17]([CH3:69])=[CH:18][C:19]([O:61]CC3C=CC=CC=3)=[C:20]([C@@H:22]3[O:51][C@H:50]([CH2:52][O:53]CC4C=CC=CC=4)[C@@H:41]([O:42]CC4C=CC=CC=4)[C@H:32]([O:33]CC4C=CC=CC=4)[C@H:23]3[O:24]CC3C=CC=CC=3)[CH:21]=2)=[CH:13][CH:12]=1)([CH3:5])[CH3:4]>[OH-].[Pd+2].[OH-].CO>[NH2:1][C:2](=[O:73])[C:3]([NH:6][C:7](=[O:72])[CH2:8][CH2:9][CH2:10][C:11]1[CH:71]=[CH:70][C:14]([CH2:15][C:16]2[C:17]([CH3:69])=[CH:18][C:19]([OH:61])=[C:20]([C@@H:22]3[O:51][C@H:50]([CH2:52][OH:53])[C@@H:41]([OH:42])[C@H:32]([OH:33])[C@H:23]3[OH:24])[CH:21]=2)=[CH:13][CH:12]=1)([CH3:5])[CH3:4]

Participants

4

Reactant 1

HCID 86638446HCID 86638446, compound

Product 1

HCID 24851758HCID 24851758, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a methanol solution (1 mL) of (1S)-1-[5-(4-[(1E)-4-[(2-amino-1,1-dimethyl-2-oxoethyl)amino]-4-oxobut-1-en-1-yl]benzyl)-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol (75 mg, 0.0765 mmol) was added 20% palladium hydroxide (15 mg), and the mixture was stirred overnight under a hydrogen atmosphere at room temperature. The reaction solution was filtered through celite, and evaporated under reduced pressure to obtain a residue. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=5:1, ethyl acetate:ethanol:water=20:2:1) to obtain the title compound (32 mg, 79%) as a colorless powder. NMR data and MS data of the compound are shown in Table 1.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customevaporated under reduced pressure
  3. customto obtain a residue
  4. customThus obtained residue was purified with silica gel column chromatography (chloroform:methanol=5:1, ethyl acetate:ethanol:water=20:2:1)

Sources & evidence

ORD record
ord-159a2bc932e1462d8a6916dbd5be3ed7
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

Loading…