2-Bromopropane → 4-(2-Isopropoxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester

HRID 1047685

반응식

HRID 1047685 반응식
[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=2[OH:20])[CH2:10][CH2:9][S:8][CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=2[O:20][CH:29]([CH3:31])[CH3:30])[CH2:6][CH2:7][S:8][CH2:9][CH2:10]1)=[O:4]

참가 물질

5

반응물 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 593142624-(2-Hydroxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester

생성물 1

HCID 593141894-(2-Isopropoxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester수율 81.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 4-(2-hydroxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester (27) (98 mg, 0.32 mmol), anhydrous Cs2CO3 (208 mg, 0.64 mmol), and KI (11 mg, 0.06 mmol) in DMF (5 mL) is added 2-bromopropane (150 μL, 1.6 mmol). The resulting reaction suspension is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (20 mL) and washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (80 g silica gel, gradient elution: 5-40% EtOAc in heptane) to give a pure product (28) as white solid (92 mg, 81%).

후처리

  1. customThe resulting reaction suspension
  2. customAfter the removal of DMF in vacuo
  3. dissolutionthe residue is dissolved in EtOAc (20 mL)
  4. washwashed with water (1×5 mL) and brine (2×5 mL)
  5. dry with materialThe organic layer is dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash column chromatography (80 g silica gel, gradient elution: 5-40% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-dc112b9fcc0246cba4432651c7307afc
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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