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Sodium Bicarbonate → 2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole

HRID 1882089
ノート
印刷プレビュー

反応式

HRID 1882089 の反応式
[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([C:25](=O)[CH2:26][CH2:27][C:28](=O)[CH:29]([C:37]2[CH:42]=[CH:41][C:40]([S:43]([CH:46]3[CH2:48][CH2:47]3)(=[O:45])=[O:44])=[CH:39][CH:38]=2)[CH2:30][CH:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[N:22][N:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:55].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([C:25]2[NH:55][C:28]([CH:29]([C:37]3[CH:42]=[CH:41][C:40]([S:43]([CH:46]4[CH2:47][CH2:48]4)(=[O:44])=[O:45])=[CH:39][CH:38]=3)[CH2:30][CH:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:27][CH:26]=2)=[N:22][N:21]=1)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 593315691-[5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

生成物 1

HCID 1361666602-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole収率 74.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

To a solution of 1-[5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (168 mg) in acetic acid (2.3 mL) was added ammonium acetate (283 mg), and the mixture was stirred at 110° C. for 1 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (122 mg, yield 74%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-59e3ce9c51e6413494d06dc09d78fc4d
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318746B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート