Diisopropylethylamine → HCID 22850667、化合物

HRID 2226604

反応式

HRID 2226604 の反応式
Br.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[C:18]([OH:20])=[O:19])=[O:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[CH2:36]([N:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:42](Cl)=[O:43])[CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:42](=[O:43])[N:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:14][C@H:13]2[C:18]([OH:20])=[O:19])=[O:11])[CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 22106956Dipentylcarbamyl chlorideHCID 70072107(S)-1-[N-(3-Chlorophenyl)-N-phenylcarbamoyl]-piperazine-2-carboxylic acid hydrobromide

生成物 1

HCID 22850667HCID 22850667、化合物収率 37.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

To a suspension of 1.05 g (2.3 mmole) of (S)-1-[N-(3-chlorophenyl)-N-phenylcarbamoyl]piperazine-2-carboxylic acid hydrobromide (from Step C) in 20 ml of methylene chloride was added 1.23 g (9.5 mmole) of N,N-diisopropylethylamine followed by the dropwise addition of a solution of 523 mg (2.38 mmole) of dipentylcarbamoyl chloride (from Example 3, Step A) in 5 ml of methylene chloride. After stirring 24 hours at 25° C., the solution was extracted with 2N HCl, then H2O and dried over MgSO4. The dried methylene chloride solution was concentrated in vacuo and the residue was dissolved in isopropyl ether and was diluted with petroleum ether (bp. 30°-60° C.) until cloudy. The oil which precipitated was then decanted, redissolved in isopropanol and concentrated in vacuo to yield 464 mg (36%) of (S)-1-[N-(3-chlorophenyl)-N-phenylcarbamoyl]-4-(dipentylcarbamoyl)piperazine-2-carboxylic acid as a glassy solid; TLC showed a single spot, Rf 0.75 (Anal tech SGF plates developed with isoamyl alcohol:acetone:water [5:2:1]).

後処理

  1. extractionthe solution was extracted with 2N HCl
  2. dry with materialH2O and dried over MgSO4
  3. concentrationThe dried methylene chloride solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in isopropyl ether
  5. additionwas diluted with petroleum ether (bp. 30°-60° C.) until cloudy
  6. customThe oil which precipitated
  7. customwas then decanted
  8. dissolutionredissolved in isopropanol
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4d8085e8ed294d1cb9ddcb558961de41
出典データセット
uspto-grants-1994_09
特許番号
US05348955

関連ノート

読み込み中…