Ethyl Acetate → HCID 178429064, compound

HRID 1009886Notes

Reaction equation

HRID 1009886 reaction equation
C(OCC)(=O)C.C(OC([NH:17][C:18]([NH:30][CH2:31]/[CH:32]=[CH:33]/[C:34]1[CH:94]=[CH:93][C:37]([CH2:38][C:39]2[C:40]([CH3:92])=[CH:41][C:42]([O:84]CC3C=CC=CC=3)=[C:43]([C@@H:45]3[O:74][C@H:73]([CH2:75][O:76]CC4C=CC=CC=4)[C@@H:64]([O:65]CC4C=CC=CC=4)[C@H:55]([O:56]CC4C=CC=CC=4)[C@H:46]3[O:47]CC3C=CC=CC=3)[CH:44]=2)=[CH:36][CH:35]=1)=[N:19]C(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[NH2:19][C:18]([NH:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:94]=[CH:93][C:37]([CH2:38][C:39]2[C:40]([CH3:92])=[CH:41][C:42]([OH:84])=[C:43]([C@@H:45]3[O:74][C@H:73]([CH2:75][OH:76])[C@@H:64]([OH:65])[C@H:55]([OH:56])[C@H:46]3[OH:47])[CH:44]=2)=[CH:36][CH:35]=1)=[NH:17]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 178428946HCID 178428946, compound

Product 1

HCID 178429064HCID 178429064, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent2×

Procedure

To a methanol (2.6 mL)-ethyl acetate (1.3 mL) mixture solution of (1S)-1-[5-[4-[(1E)-3-[[benzyloxy carbonyl amino(benzyloxycarbonylimino)methyl]amino]prop-1-en-1-yl]benzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol (154 mg, 0.131 mmol) was added 20% palladium hydroxide (160 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through celite, and evaporated under reduced pressure to obtain a residue. Thus obtained residue was dissolved in methanol (1.5 mL). And 20% palladium hydroxide (63 mg) was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 days. 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 (ethyl acetate:ethanol:water=10:2:1 then 5:2:1, and then ethanol:water=10:1) to obtain the title compound (38 mg, 63%) 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. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 2 days
  5. filtrationThe reaction solution was filtered through celite
  6. customevaporated under reduced pressure
  7. customto obtain a residue
  8. customThus obtained residue was purified with silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-6bda05ea311e46dc9faca65e273341d5
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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