Diisopropylethylamine → HCID 89851371、化合物

HRID 627086ノート

反応式

HRID 627086 の反応式
[CH2:1]([O:4][NH:5][C@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([NH2:14])=[O:13])[CH:8]=[C:7]1[CH3:15])[CH:2]=[CH2:3].[CH2:16]([O:19]N[C@H]1CN[C@@H](C(N)=O)C=C1C)C=C.C(N(CC)C(C)C)(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]1[C:16](=[O:19])[N:10]2[CH2:11][C@H:6]1[C:7]([CH3:15])=[CH:8][C@H:9]2[C:12]([NH2:14])=[O:13])[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 94429Triphosgene2 回HCID 89851806(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide2 回HCID 89852356(2S,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

生成物 1

HCID 89851371HCID 89851371、化合物収率 64.8%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide and (2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 22, 0.429 g, 2.03 mmol) and N,N-diisopropylethylamine (1.415 mL, 8.12 mmol) in acetonitrile (170 mL) at 0° C. was added triphosgene (0.241 g, 0.81 mmol) as a solution in acetonitrile (1.5 mL). The triphosgene solution was added at a rate of 0.1 mL/min. Once addition was complete the reaction was warmed to room temperature and stirred over weekend. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded (2S,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (0.312 g, 64.8%) as a light yellow oil.

後処理

  1. additionOnce addition
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-73b26f40baac4b7fa0d3ec75c0000028
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

読み込み中…