Cadaverine → 1-[5-[N-(2-n-propyl-n-pentanoyl)glycyl]-amino-n-pentylcarbamoyl]-5-fluorouracil

HRID 728620ノート

反応式

HRID 728620 の反応式
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C(Cl)(Cl)=O.C(C(CCC)C(NC[C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]N)=[O:23])=O)CC.[NH2:34]CCCCCN.[CH2:41]([CH:44]([CH2:52][CH2:53][CH3:54])[C:45]([NH:47][CH2:48][C:49]([OH:51])=O)=[O:46])[CH2:42][CH3:43].C(N(CC)CC)C>N1C=CC=CC=1>[CH2:52]([CH:44]([CH2:41][CH2:42][CH3:43])[C:45]([NH:47][CH2:48][C:49]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:24]([NH2:34])[C:22]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])=[O:23])=[O:51])=[O:46])[CH2:53][CH3:54]

参加物

8

反応物 6

HCID 273CadaverineHCID 33855-FluorouracilHCID 6371PhosgeneHCID 8471TriethylamineHCID 1819192-(2-propylpentanoylamino)acetic AcidHCID 53710869N-[N-(2-n-propyl-n-pentanoyl)glycyl]pentamethylenediamine

生成物 1

HCID 679257401-[5-[N-(2-n-propyl-n-pentanoyl)glycyl]-amino-n-pentylcarbamoyl]-5-fluorouracil

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

In a solution of 1.09 g (8.42 mmole) of 5-fluorouracil dissolved in 30 ml of pyridine was blown 0.75 g (7.58 mmole) of phosgene in the same manner as described in Example 7 to conduct the reaction. A yellowish crystals-suspended liquor thus prepared was stirred for one hour under cooling. Under substantially the same conditions as in Example 7, to this suspension was added dropwise a solution comprising 1.93 g (6.76 mmole) of N-[N-(2-n-propyl-n-pentanoyl)glycyl]pentamethylenediamine synthesized by reacting pentamethylenediamine and N-(2-propyl-n-pentanoyl)glycine under substantially the same conditions described in Reference example 12 and 1.53 g (15.16 mmole) of triethylamine dissolved in 20 ml pyridine to conduct the reaction. After treating the reaction mixture in the same manner as described in Example 7, by using the same developing solvent as described in Example 7, fractions which seem to be the title compound were collected. 1.15 g (Yield: 38.5%) of pale yellow crystals were obtained. A part of the crystals was purified again by using silica gel column chromatography with the same developing solvent to give pure 1-[5-[N-(2-n-propyl-n-pentanoyl)glycyl]amino-n-pentylcarbamoyl]-5-fluorouracil as colorless crystals.

後処理

  1. customthe reaction
  2. customA yellowish crystals-suspended liquor thus prepared
  3. temperatureunder cooling
  4. customsynthesized
  5. customthe reaction
  6. additionAfter treating the reaction mixture in the same manner

出典と根拠

ORDレコード
ord-c08ae982785e4476bcc197e50372f70f
出典データセット
uspto-grants-1991_09
特許番号
US05049551

反応ノート

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