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4-Methylmorpholine → 6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N-(2-oxopropyl)pyridazine-3-carboxamide

HRID 46200
ノート
印刷プレビュー

反応式

HRID 46200 の反応式
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25]C3C=CC=CC=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11](O)=[O:12])=[CH:7][CH:6]=1.F[C:58](F)(F)[C:59]([OH:61])=O.[NH2:64][CH2:65]C(=O)C.CCN=C=NCCCN(C)C.O.ON1[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][C:85]=2N=N1.CN1CCOCC1>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25][C:85]3[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11]([NH:64][CH2:65][C:59](=[O:61])[CH3:58])=[O:12])=[CH:7][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 672878076-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acidHCID 866644281-Aminopropan-2-one trifluoroacetic acid salt

生成物 1

HCID 67288316
6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N-(2-oxopropyl)pyridazine-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acid (1.2 mmol), 1-aminopropan-2-one trifluoroacetic acid salt (346 mg, 1.9 mmol), EDCI (472 mg, 2.5 mmol), and 1-hydroxybenzotriazole hydrate (478 mg, 3.1 mmol) in N,N-dimethylformamide (10 mL) was added 4-methylmorpholine (0.68 mL, 6.2 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine prior to drying over magnesium sulfate. Filtration through a plug of silica gel and removal of the volatiles under reduced pressure yielded titled compound as a brown amorphous solid, which was used without further purification.

後処理

  1. washAfter dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine
  2. dry with materialto drying over magnesium sulfate
  3. filtrationFiltration
  4. customthrough a plug of silica gel and removal of the volatiles under reduced pressure

出典と根拠

ORDレコード
ord-1212c87af3bb44879fb9252dec74a92d
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08541380B2

反応ノート

読み込み中…

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