Ethanol → HCID 11799355, compound

HRID 1683952Notes

Reaction equation

HRID 1683952 reaction equation
C(OC([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:31][OH:32])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=O)C1C=CC=CC=1.C(O)C.C1COCC1.[C:41]1([S:51](Cl)(=[O:53])=[O:52])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1>CN(C)C=O.CN(C1C=CN=CC=1)C.[C].[Pd]>[C:41]1([S:51]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:31][OH:32])[CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])(=[O:53])=[O:52])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 665601-Naphthalenesulfonyl chlorideHCID 10836729HCID 10836729, compound

Product 1

HCID 11799355HCID 11799355, compoundYield 82.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-benzyloxycarbonyl-(L)-isoleucyl-(L)-tryptophanol (55 g), palladium-carbon (5%, 50% wet, 30 g) and ethanol (50 ml)-THF (300 ml) was subjected to catalytic hydrogenation at room temperature and atmospheric pressure. After the catalyst was filtered off, the filterate was concentrated under reduced pressure to yield an oily substance. The oil was dissolved in N,N-dimethylformamide (300 ml), and 1-naphthalenesulfonyl chloride (30 g) and 4-(N,N-dimethylamino)pyridine (DMAP) (17 g) were added to the ice-cooling mixture. After stirring at 0° C. for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was suspended in ethyl acetate and the mixture was successively washed with 10% aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate and brine, and dried (MgSO4). The organic solvent was evaporated off and the residual oil was purified by column chromatography on silica gel. Elution with ethyl acetate-hexane (3:2,v/v) gave N-(1-naphthylsulfonyl)-(L)-isoleucyl-(L)-tryptophanol (51 g, 82%) as crystals.

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filterate was concentrated under reduced pressure
  4. customto yield an oily substance
  5. temperaturecooling mixture
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. washthe mixture was successively washed with 10% aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate and brine
  8. dry with materialdried (MgSO4)
  9. customThe organic solvent was evaporated off
  10. customthe residual oil was purified by column chromatography on silica gel
  11. washElution with ethyl acetate-hexane (3:2,v/v)

Sources & evidence

ORD record
ord-8a30d3fa17234cc59fa1e505956822b4
Source dataset
uspto-grants-1997_06
Patent number
US05639781

Reaction notes

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