Sulfuryl chloride → HCID 68508325、化合物

HRID 221937ノート

反応式

HRID 221937 の反応式
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[CH:46]=[C:45]3[C:48]([CH2:55][C:56]4[CH:61]=[CH:60][C:59]([CH2:62][CH3:63])=[CH:58][CH:57]=4)=[C:49]([Si](C)(C)C)[S:50][C:44]3=[CH:43][C:42]=1[CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:67])(=O)=O.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[CH:46]=[C:45]3[C:48]([CH2:55][C:56]4[CH:61]=[CH:60][C:59]([CH2:62][CH3:63])=[CH:58][CH:57]=4)=[C:49]([Cl:67])[S:50][C:44]3=[CH:43][C:42]=1[CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 68503973HCID 68503973、化合物

生成物 1

HCID 68508325HCID 68508325、化合物収率 43.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(3′R,4′S,5S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-3-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-2-trimethylsilyl-spiro[thieno[2,3,f]isobenzofuran-5(7H),2′-[2H]pyran] (0.122 g, 0.139 mmol) was dissolved in acetonitrile (0.93 mL). Sulfuryl chloride (20.6 mg, 0.153 mmol) was added to the resultant solution, and then the solution was stirred for 3.5 hours at room temperature. Saturated aqueous sodium hydrogen carbonate was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:11.5)), to thereby obtain the titled compound (50.2 mg, 43%).

後処理

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:11.5))

出典と根拠

ORDレコード
ord-a37abb554813427cb2a4b93628e52cbb
出典データセット
uspto-grants-2012_06
特許番号
US08207134B2

反応ノート

読み込み中…