1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18337567、化合物

HRID 1760822ノート

反応式

HRID 1760822 の反応式
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

参加物

8

反応物 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

生成物 1

HCID 18337567HCID 18337567、化合物収率 47.4%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c090ae82ad540489dc4833ca4ad7a9c
出典データセット
uspto-grants-2005_01
特許番号
US06844366B2

反応ノート

読み込み中…