Potassium Carbonate → HCID 13269245、化合物

HRID 638318ノート

反応式

HRID 638318 の反応式
Cl.[OH:2]/[N:3]=[C:4](/[C:10]1[N:11]=[C:12]([NH:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:13][CH:14]=1)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:35]1([CH2:38]Br)[CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:35]1([CH2:38][O:2]/[N:3]=[C:4](/[C:10]2[N:11]=[C:12]([NH:15][C:16]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:13][CH:14]=2)\[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:37][CH2:36]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 9589415(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate hydrochloride

生成物 1

HCID 13269245HCID 13269245、化合物収率 67.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Ethyl (Z)-2-hydroxyimino-2-(2-tritylaminothiazol-4-yl)acetate, hydrochloride salt (30 g) was stirred with cyclopropylmethyl bromide (13.5 g) in dimethylsulphoxide (150 ml) containing potassium carbonate (30 g) under nitrogen at 21° for 7 hours. The mixture was partitioned between methylene chloride and water. The aqueous layer was extracted with more methylene chloride and the combined organic solutions were washed with water. After drying with magnesium sulphate, the solution was concentrated and loaded onto a column of Sorbsil U30 silica gel (200 g). The column was eluted with ethyl acetate (10 to 30%) in petroleum ether (b.p. 40°-60°). Evaporation of appropriate fractions gave the title compound (20.9 g); λmax (ethanol) 234.5 nm (E1 cm1% 403); λinf. 254.5 nm (E1 cm1% 302), 259.5 nm (E1 cm1% 267), 265 nm (E1 cm1% 229), 271.5 nm (E1 cm1% 190) and 294 nm (E1 cm1% 111); νmax (CHBr3) 3398 (NH), 1730 (ester), and 1593 and 1491 cm-1 (aromatic double bond).

後処理

  1. customThe mixture was partitioned between methylene chloride and water
  2. extractionThe aqueous layer was extracted with more methylene chloride
  3. washthe combined organic solutions were washed with water
  4. dry with materialAfter drying with magnesium sulphate
  5. concentrationthe solution was concentrated
  6. washThe column was eluted with ethyl acetate (10 to 30%) in petroleum ether (b.p. 40°-60°)
  7. customEvaporation of appropriate fractions

出典と根拠

ORDレコード
ord-445e56e6879d478faaebcc110c97179e
出典データセット
uspto-grants-1985_12
特許番号
US04560683

反応ノート

読み込み中…