Tetrahydrofuran → HCID 14209149、化合物

HRID 279778ノート

反応式

HRID 279778 の反応式
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[CH2:8][CH:7]1[C:11](O)=O.C(N(CC)CC)C.[N+](=C)=[N-].[N+](=CC(C1N(CC2C=CC(OC)=CC=2OC)[C:37](=[O:50])C1)=O)=[N-].[O:51]1CCCC1>C(OCC)C>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[CH2:8][CH:7]1[CH2:11][C:37]([OH:50])=[O:51]

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9550DiazomethaneHCID 14209146HCID 14209146、化合物HCID 54501513HCID 54501513、化合物

生成物 1

HCID 14209149HCID 14209149、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-15 °C

実験手順

13.2 g (50 millimoles) of 1-(2,4-dimethoxy-benzyl)-4-oxo-2-azetidine-carboxylic acid prepared according to the preceding paragraph are dissolved in 150 ml of anhydrous tetrahydrofurane and to the solution first 7.3 ml (52.5 millimole) of triethylamine and thereafter under stirring and ice-cooling 5.0 ml (52.5 millimoles) of ethylchloroformiate are added. The mixture is cooled to -15° C., stirred at this temperature for 20 minutes and the precipitated triethylamine salt is filtered off under argon. To the filtrate a solution of 22.5 g (150 millimole) diazomethane and 230 ml of cold diethyl ether is added. The solution is stirred, allowed to warm to ambient temperature and after 2 hours the mixture is evaporated to dryness. The residue is dissolved in 20 ml of benzene and subjected to column chromatography (adsorbent: 150 g of Kieselgel G, diameter 0.063-0.2000 mm; eluant: benzene-acetone 7:2). On rubbing with ether a crystalline product is obtained. Yield: 10.5 g (73%) of 4-diazoacetyl-1-(2,4-dimethoxy-benzyl)-2-azetidinone, m.p.: 90°-91° C.

後処理

  1. temperatureice-cooling 5.0 ml (52.5 millimoles) of ethylchloroformiate
  2. additionare added
  3. stirringstirred at this temperature for 20 minutes
  4. filtrationthe precipitated triethylamine salt is filtered off under argon
  5. stirringThe solution is stirred
  6. temperatureto warm to ambient temperature and after 2 hours the mixture
  7. customis evaporated to dryness
  8. dissolutionThe residue is dissolved in 20 ml of benzene
  9. customis obtained

出典と根拠

ORDレコード
ord-89dfed38b0914e05b5df6165c7a8b419
出典データセット
uspto-grants-1986_05
特許番号
US04587049

反応ノート

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