Ethanethioic acid, S-phenyl ester → HCID 86722000、化合物

HRID 1398030ノート

反応式

HRID 1398030 の反応式
N1([C:10]([CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)=[O:11])C2C=CC=CC=2N=N1.CCOCC.[Mg+2].[Br-].[Br-].[C:30]([S:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:32])[CH3:31].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:34]1([S:33][C:30](=[O:32])[CH2:31][C:10](=[O:11])[CH:12]2[CH2:13][C:14]([CH3:20])([CH3:21])[O:15][C:16]([CH3:18])([CH3:19])[CH2:17]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

6

反応物 4

HCID 13630Ethanethioic acid, S-phenyl esterHCID 81531DiisopropylethylamineHCID 9903262Magnesium bromide diethyl etherateHCID 86721999Benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone

生成物 1

HCID 86722000HCID 86722000、化合物収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone (1.70 g, 5.62 mmol), magnesium bromide diethyl etherate (4.14 g, 16.06 mmol), and S-phenyl thioacetate (0.76 mL, 5.35 mmol) in 21 mL of DCM at RT was added dropwise DIEA (3.95 mL, 21.41 mmol). The mixture was stirred overnight and then diluted with 50 mL of DCM and washed with 1N HCl (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, concentrated, and the residue purified by flash chromatography on silica gel to give 1.2 g (70%) of a colorless oil. Mass spectrum (ESI, m/z): Calculated for C18H24O3S, 321.1 (M+H), found 321.1.

後処理

  1. washwashed with 1N HCl (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-6e58a00dde9744429f0684c3aa76e09d
出典データセット
uspto-grants-2014_12
特許番号
US08901314B2

反応ノート

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