Triethylamine → (6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1390410노트

반응식

HRID 1390410 반응식
P(Cl)(Cl)(Cl)(Cl)Cl.[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12](=[N:16][O:17][CH3:18])[C:13]([OH:15])=O.[NH2:19][C@@H:20]1[C:39](=[O:40])[N:22]2[C:23]([C:36]([OH:38])=[O:37])=[C:24]([CH2:27][O:28][C:29](=[O:35])[NH:30]C(=O)CCl)[CH2:25][S:26][C@H:21]12.C(N(CC)CC)C>ClCCl.CO.CN(C)C(=O)C>[C:29]([O:28][CH2:27][C:24]1[CH2:25][S:26][C@@H:21]2[C@H:20]([NH:19][C:13](=[O:15])[C:12]([C:8]3[O:7][CH:11]=[CH:10][CH:9]=3)=[N:16][O:17][CH3:18])[C:39](=[O:40])[N:22]2[C:23]=1[C:36]([OH:38])=[O:37])(=[O:35])[NH2:30]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 2724574alpha-(Methoxyimino)furan-2-acetic acidHCID 12884123(6R,7R)-7-amino-3-chloroacetylcarbamoyloxymethylceph-3-em-4-carboxylic acid

생성물 1

HCID 41375(6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid수율 90.3%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매2회HCID 31374Dimethylacetamide용매

실험 절차

N,N-Dimethylacetamide (1.5 ml) was added to a solution of phosphorus pentachloride (750 mg, 3.6 mmole) in anhydrous dichloromethane (15 ml) cooled to -10°. After 10 minutes, 2-(fur-2-yl)-2-methoxyiminoacetic acid (syn isomer) (612 mg, 3.6 mmole) was added to the resulting suspension, which soon became a clear solution and was stirred at -10° for 15 minutes. Ice (3 g) was added and after 10 minutes the layers were allowed to separate in a dropping funnel. The organic phase was slowly (over 5 minutes) run into a cooled (-10°) solution of (6R,7R)-7-amino-3-chloroacetylcarbamoyloxymethylceph-3-em-4-carboxylic acid (1.05 g, 3 mmole) in dichloromethane (15 ml) containing triethylamine (0.9 ml, 6.5 mmole). Methanol (1 ml) was added after 40 minutes, and 5 minutes later the reaction mixture was extracted twice with 3% w/v aqueous sodium bicarbonate solution (150 ml). The aqueous extract was washed with ethyl acetate (25 ml) and left at 20° for 4 hours. The solution was washed twice with ethyl acetate, acidified with 2N-hydrochloric acid, and extracted 3 times with ethyl acetate. The combined organic layers were dried over magnesium sulphate, decolourised with activated charcoal, and evaporated in vacuo to give a pale-yellow solid (1.15 g, 87%). This was washed with diethyl ether and filtered off to give the title compound (0.91 g, 71%); λmaxpH6 274 nm (ε 17,300). The IR and NMR spectra of the product agreed with those of an authentic sample.

후처리

  1. temperaturecooled to -10°
  2. customto separate in a dropping funnel
  3. custom(over 5 minutes)
  4. extraction5 minutes later the reaction mixture was extracted twice with 3% w/v aqueous sodium bicarbonate solution (150 ml)
  5. extractionThe aqueous extract
  6. washwas washed with ethyl acetate (25 ml)
  7. waitleft at 20° for 4 hours
  8. washThe solution was washed twice with ethyl acetate
  9. extractionextracted 3 times with ethyl acetate
  10. dry with materialThe combined organic layers were dried over magnesium sulphate
  11. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-6ef8abb8a6944eaca75ca8c013aaeaa9
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04138555

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