Pyridine → HCID 70605506、化合物

HRID 614135ノート

反応式

HRID 614135 の反応式
[C:1]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29](=O)[NH:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[Si:49]([CH3:52])([CH3:51])[CH3:50].C(Cl)(Cl)=O.[N-:57]=[N+:58]=[N-:59].CN(C)C(=[NH2+])N(C)C.[OH-].[Na+]>O.C(Cl)(Cl)Cl>[C:1]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29]4[N:30]([CH2:31][C:32]5[CH:37]=[CH:36][C:35]([O:38][Si:49]([CH3:52])([CH3:51])[CH3:50])=[CH:34][CH:33]=5)[N:59]=[N:58][N:57]=4)[C:25]([CH3:27])([CH3:28])[S:26][C@H:22]23)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

9

反応物 6

HCID 1049PyridineHCID 6371PhosgeneHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 70604879HCID 70604879、化合物HCID 178484365HCID 178484365、化合物

生成物 1

HCID 70605506HCID 70605506、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒2 回

反応条件

温度
4 °C

実験手順

To a stirred solution of 1.69 g. (3 m mole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-hydroxybenzyl]carbamoyl)penam prepared as described in Example XIII in 9 ml. of chloroform is added 1 ml. (12 mmole) of pyridine. The solution is cooled to ca. 4° C. in an ice-bath and 0.80 ml. of chlorotrimethylsilane is added. The solution is stirred for 40 minutes at ambient temperature, and then it is again cooled to ca. 4° C. Phosgene (1.5 ml. of a 4.3 M solution in chloroform 6.45 mmole) is added and the cooling bath is removed. Stirring is continued for a further 1.5 hours, and then all the volatile components are removed by evaporation in vacuo. The oily residue is redissolved in 6 ml. of chloroform and the solution is cooled to ca. 4° C. in an ice-bath. To the stirred solution is added 0.95 g. (6 mmole) of tetramethylguanidinium azide, and then stirred is continued for a further 1 hour at ambient temperature. At this point, 25 ml. of water is added, followed by sufficient 1N sodium hydroxide to bring the pH of the aqueous phase to 10. The chloroform layer is removed, washed with water, dried using sodium sulfate, and evaporated to dryness in vacuo. This affords crude 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[4-trimethylsilyloxybenzyl]tetrazol-5-yl)penam, which is purified by chromatography on silica gel using chloroform as eluant.

後処理

  1. temperatureit is again cooled to ca. 4° C
  2. customthe cooling bath is removed
  3. stirringStirring
  4. waitis continued for a further 1.5 hours
  5. customall the volatile components are removed by evaporation in vacuo
  6. dissolutionThe oily residue is redissolved in 6 ml
  7. temperatureof chloroform and the solution is cooled to ca. 4° C. in an ice-bath
  8. additionTo the stirred solution is added 0.95 g
  9. waitis continued for a further 1 hour at ambient temperature
  10. customThe chloroform layer is removed
  11. washwashed with water
  12. customdried
  13. customevaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-1a5ad4fff2ac4543873c0da55fcd9fe1
出典データセット
uspto-grants-1979_03
特許番号
US04143039

反応ノート

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