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1-(Cyclopentylsulfonyl)-3-iodobenzene → (5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2118340
ノート
印刷プレビュー

反応式

HRID 2118340 の反応式
[CH3:1][C:2]1([CH3:30])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][C:28]#[CH:29])[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[CH:31]1([S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41](I)[CH:40]=2)(=[O:38])=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1>CC#N.C(N(CC)CC)C>[CH:31]1([S:36]([C:39]2[CH:40]=[C:41]([C:29]#[C:28][CH2:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:14]3[CH2:13][C@@H:12]([C:10]4[CH:9]=[CH:8][C:6]5[O:7][C:2]([CH3:30])([CH3:1])[O:3][CH2:4][C:5]=5[CH:11]=4)[O:16][C:15]3=[O:17])[CH:42]=[CH:43][CH:44]=2)(=[O:37])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 691197141-(Cyclopentylsulfonyl)-3-iodobenzeneHCID 86607678(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-pentyn-1-yloxy)hexyl]-1,3-oxazolidin-2-one

生成物 1

HCID 69119922(5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one収率 78.2%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 8471
Triethylamine
溶媒

実験手順

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-pentyn-1-yloxy)hexyl]-1,3-oxazolidin-2-one (207 mg) and 1-(cyclopentylsulfonyl)-3-iodobenzene (Example 8iii.) (202 mg) in MeCN (8 ml) and triethylamine (4 ml) was deoxygenated by bubbling a nitrogen stream through for 10 min. Copper (I) iodide (10 mg) and dichlorobis(triphenylphosphine)palladium (II) (18 mg) were added and the mixture stirred at 20° for 4 h. The solvent was evaporated in vacuo and the residues purified by using a SPE silica bond elut cartridge (10 g, silica). Elution with DCM (1vol), EtOAc-cyclohexane (1:4) (3vols), (1:3) (1vol) then (1:1) (3vols) gave the title compound (243 mg). LCMS RT=3.79 min.

後処理

  1. customby bubbling a nitrogen stream through for 10 min
  2. additionCopper (I) iodide (10 mg) and dichlorobis(triphenylphosphine)palladium (II) (18 mg) were added
  3. customThe solvent was evaporated in vacuo
  4. customthe residues purified
  5. washElution with DCM (1vol), EtOAc-cyclohexane (1:4) (3vols), (1:3) (1vol)

出典と根拠

ORDレコード
ord-6dd2f8f0243e4113a17220fff5ea6095
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07442839B2

反応ノート

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