Potassium Carbonate → HCID 13269245, 화합물

HRID 638318노트

반응식

HRID 638318 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 13269245HCID 13269245, 화합물수율 67.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-445e56e6879d478faaebcc110c97179e
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560683

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