Ethanethioic acid, S-phenyl ester → HCID 86722000, 화합물

HRID 1398030노트

반응식

HRID 1398030 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 86722000HCID 86722000, 화합물수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6e58a00dde9744429f0684c3aa76e09d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901314B2

반응 노트

불러오는 중…