Aluminum(III) Chloride → HCID 178508516, 화합물

HRID 1707474노트

반응식

HRID 1707474 반응식
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:63])[C@@H:24]([NH:25][C:26](=[O:62])/[C:27](/[C:49]4[N:50]=[C:51]([NH:54]C(OC(C)(C)C)=O)[S:52][CH:53]=4)=[N:28]\[O:29]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:64][S:65][C:66]2[N:67]=[N:68][NH:69][CH:70]=2)=[S:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(OC)C=CC=CC=1.[N+](C)([O-])=O>[NH2:54][C:51]1[S:52][CH:53]=[C:49](/[C:27](=[N:28]/[OH:29])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:63])[N:22]3[C:17]([C:15]([OH:14])=[S:16])=[C:18]([CH2:64][S:65][C:66]4[N:67]=[N:68][NH:69][CH:70]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

참가 물질

5

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 178452987HCID 178452987, 화합물

생성물 1

HCID 178508516HCID 178508516, 화합물수율 93.4%

시약·촉매·용매 2

HCID 6375Nitromethane용매HCID 7519Anisole용매2회

실험 절차

To a suspension of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(1,2,3-triazol-4-yl) thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (9.2 g: 9 mMol.) in a mixture of anisole (18 ml) and nitromethane (72 ml) is added dropwise a solution of aluminum chloride (9.6 g: 72 mMol.) in anisole (31 ml) at -30° C. After stirring for 1 hour at the same temperature, the reaction mixture is quenched with ethanol (25 ml), stirred for several minutes, diluted with 1N-hydrochloric acid (75 ml) and water (500 ml), and washed with ethyl acetate. The aqueous layer was separated, concentrated to remove the organic solvents, and passed through a column of styrene-divinylbenzene copolymer adsorbent. The product is eluted with a mixture of methanol and water (4:1) to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid as pale yellow powder (4.19 g). Yield: 90%.

후처리

  1. customthe reaction mixture is quenched with ethanol (25 ml)
  2. stirringstirred for several minutes
  3. additiondiluted with 1N-hydrochloric acid (75 ml) and water (500 ml)
  4. washwashed with ethyl acetate
  5. customThe aqueous layer was separated
  6. concentrationconcentrated
  7. customto remove the organic solvents
  8. washThe product is eluted with a mixture of methanol and water (4:1)

출처 및 근거

ORD 기록
ord-e6bed7ea83814f6899f3677782e7ee1f
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05352792

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