Triacetoxyperiodinane → 5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole-2-carbaldehyde

HRID 1882104ノート

反応式

HRID 1882104 の反応式
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:30][C:29]([CH2:31][OH:32])=[N:28][N:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>C(#N)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:30][C:29]([CH:31]=[O:32])=[N:28][N:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 136166657[5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanol

生成物 1

HCID 1361666495-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole-2-carbaldehyde収率 100.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of [5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanol (700 mg) in acetonitrile (10 mL) was added Dess-Martin reagent (752 mg), and the mixture was stirred at 80° C. for 30 min. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was stirred for 20 min. The insoluble material was removed by filtration through celite, and the filtrate was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (700 mg, yield 100%) as a yellow amorphous solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred for 20 min
  3. customThe insoluble material was removed by filtration through celite
  4. additionthe filtrate was diluted with ethyl acetate
  5. washwashed with water
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0d241d82ff434138b1345f31e03a3c41
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

読み込み中…