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Dimethyl Sulfoxide → HCID 57254734、化合物

HRID 2082620
ノート
印刷プレビュー

反応式

HRID 2082620 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([CH:13]1[CH:39]=[C:38]([CH3:40])[CH:37]([F:41])[CH:36]([CH3:42])[CH2:35][CH:34]([O:43][CH3:44])[CH:33]2[O:45][C:29]([OH:49])([CH:30]([CH3:48])[CH2:31][CH:32]2[O:46][CH3:47])[C:28](=[O:50])[C:27](=[O:51])[N:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[C:20](=[O:52])[O:19][CH:18]([C:53]([CH3:64])=[CH:54][CH:55]2[CH2:60][CH2:59][CH:58]([OH:61])[CH:57]([O:62][CH3:63])[CH2:56]2)[CH:17]([CH3:65])[CH:16]([O:66][Si:67]([CH:74]([CH3:76])[CH3:75])([CH:71]([CH3:73])[CH3:72])[CH:68]([CH3:70])[CH3:69])[CH2:15][C:14]1=[O:77])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([CH:13]1[CH:39]=[C:38]([CH3:40])[CH:37]([F:41])[CH:36]([CH3:42])[CH2:35][CH:34]([O:43][CH3:44])[CH:33]2[O:45][C:29]([OH:49])([CH:30]([CH3:48])[CH2:31][CH:32]2[O:46][CH3:47])[C:28](=[O:50])[C:27](=[O:51])[N:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[C:20](=[O:52])[O:19][CH:18]([C:53]([CH3:64])=[CH:54][CH:55]2[CH2:60][CH2:59][C:58](=[O:61])[CH:57]([O:62][CH3:63])[CH2:56]2)[CH:17]([CH3:65])[CH:16]([O:66][Si:67]([CH:74]([CH3:76])[CH3:75])([CH:71]([CH3:73])[CH3:72])[CH:68]([CH3:70])[CH3:69])[CH2:15][C:14]1=[O:77])[CH3:12]
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

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57141870HCID 57141870、化合物

生成物 1

HCID 57254734HCID 57254734、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
-78 °C

実験手順

To a cooled solution (-78° C.) of oxalyl chloride (1.5 ml of 2M solution in CH2Cl2) is added dimethyl sulfoxide (361 mg) dropwise, followed by a solution of 17-ethyl-20-fluoro-1-hydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-14-triisopropylsilyloxy-23,25-dimethoxy-13,19,21, 27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ] octacos-18-ene-2,3,10,16-tetraone (947 mg) in dry methylene chloride (3 ml). The reaction mixture is stirred for 30 min. at -78° C. and then triethylamine (1 ml) is added. The reaction temperature is raised to room temperature, reaction is poured into water (20 ml), and extracted with ethyl acetate (three times). Combined organic layers are washed (water, sat'd NaHCO3), dried (anhydrous Na2SO4), and filtered. Removal of solvent followed by purification (silica gel column chromatography), gives the title compound.

後処理

  1. temperatureThe reaction temperature is raised to room temperature
  2. customreaction
  3. extractionextracted with ethyl acetate (three times)
  4. washCombined organic layers are washed (water, sat'd NaHCO3)
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. customRemoval of solvent
  8. customfollowed by purification (silica gel column chromatography)

出典と根拠

ORDレコード
ord-cbaead0a0f0a4aca9734d5d781fbe38e
出典データセット
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05189042

反応ノート

読み込み中…

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