Tetrahydrofuran → HCID 54110952, 화합물

HRID 618734노트

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HRID 618734 반응식
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[NH:5][C:6](=[O:23])[C@H:7]([C@H:19]([CH2:21][CH3:22])[CH3:20])[NH:8]C(OCC1C=CC=CC=1)=O.C1COCC1.[C:40]1([S:50](Cl)(=[O:52])=[O:51])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1>CN(C)C=O.CN(C1C=CN=CC=1)C.[C].[Pd]>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[NH:5][C:6](=[O:23])[C@H:7]([C@H:19]([CH2:21][CH3:22])[CH3:20])[NH:8][S:50]([C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1)(=[O:52])=[O:51]

참가 물질

7

반응물 3

HCID 8028TetrahydrofuranHCID 665601-Naphthalenesulfonyl chlorideHCID 21074402CARBOBENZYLOXY-L-ISOLEUCYL-L-TRYPTOPHAN METHYL ESTER

생성물 1

HCID 54110952HCID 54110952, 화합물수율 77.4%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 178418390HCID 178418390, 화합물촉매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A mixture of N-benzyloxycarbonyl-(L)-isoleucyl-(L)-tryptophan methyl ester (11.3 g), palladium-carbon (5%, 50% wet, 3.0 g) and THF (50 ml) was subjected to catalytic hydrogenation at room temperature and atomospheric pressure. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure to yield an oily substance. The oil was dissolved in N,N-dimethylformamide (50 ml), and 1-naphthalenesulfonyl chloride (5.8 g) and 4-(N,N-dimethylamino)pyridine (DMAP) (3.2 g) were added to the ice-cooling mixture. After stirring at 0° C. for 3 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 to yield N-(1-naphthylsulfonyl)-(L)-isoleucyl-(L)-tryptophan methyl ester (9.8 g, 77%) as crystals. Melting point: 172-174° C.

후처리

  1. customwas subjected to catalytic hydrogenation at room temperature
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate 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

출처 및 근거

ORD 기록
ord-fe17f9b960b84a2bb61c702148ba40ee
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955491

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