1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18337567, 화합물

HRID 1760822노트

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HRID 1760822 반응식
C1OC2C=CC(C[O:7][C:8](=O)[C@H:9]([N:20]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]4[O:42][CH2:43][O:44][C:38]=4[CH:37]=3)[S:21]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([O:31][CH3:32])=[C:26]([CH3:33])[C:25]=3[CH3:34])(=[O:23])=[O:22])[C@@H:10]([O:12][Si](CC)(CC)CC)[CH3:11])=CC=2O1.[CH2:50]([O:57][NH2:58])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(OCC)(=O)C.[Pd].C(O)C.O1CCCC1>[CH2:50]([O:57][NH:58][C:8](=[O:7])[C@H:9]([N:20]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]2[O:42][CH2:43][O:44][C:38]=2[CH:37]=1)[S:21]([C:24]1[C:29]([CH3:30])=[CH:28][C:27]([O:31][CH3:32])=[C:26]([CH3:33])[C:25]=1[CH3:34])(=[O:23])=[O:22])[C@@H:10]([OH:12])[CH3:11])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 102313O-BenzylhydroxylamineHCID 865900272(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzene-sulfonyl)amino]-3(S)-(triethylsilyloxy)butyric acid 3,4-methylenedioxybenzyl ester

생성물 1

HCID 18337567HCID 18337567, 화합물수율 47.4%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

To a solution of 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-(triethylsilyloxy)butyric acid 3,4-methylenedioxybenzyl ester (3.3 g, 4.62 mmol) in argon deoxygenated 80% ethanol-tetrahydrofuran (100 mL) was added 10% Pd—C (2 g) and the resulting reaction mixture was hydrogenated at atmospheric pressure for 45 min. The reaction mixture was degassed under argon, the slurry was filtered over Celite, and the Celite pad was washed with ample 80% ethanol-methylene chloride. The filtrate was concentrated and azeotroped with tetrahydrofuran (200 mL) and the residue was dissolved in dimethylformamide (25 mL). O-Benzyl hydroxylamine (2.0 g, 16.2 mmol), HOBT (0.71 g, 5.2 mmol), and EDAC (3.1 g, 16.2 mmol) were added and the reaction mixture was stirred for 16 h. The reaction mixture was diluted with ethyl acetate and was washed with 2.4 N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate. The mixture was then dried over magnesium sulfate and concentrated in vacuo to afford crude N-benzyloxy-2(R)-[(3,4-methylenedioxy-benzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-hydroxybutyramide (1.25 g) which was taken directly into the next reaction without further purification.

후처리

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was degassed under argon
  3. filtrationthe slurry was filtered over Celite
  4. washthe Celite pad was washed with ample 80% ethanol-methylene chloride
  5. concentrationThe filtrate was concentrated
  6. customazeotroped with tetrahydrofuran (200 mL)
  7. dissolutionthe residue was dissolved in dimethylformamide (25 mL)
  8. washwas washed with 2.4 N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate
  9. dry with materialThe mixture was then dried over magnesium sulfate
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8c090ae82ad540489dc4833ca4ad7a9c
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844366B2

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