Diisopropylethylamine → HCID 22850667, 화합물

HRID 486755

반응식

HRID 486755 반응식
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

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 22106956Dipentylcarbamyl chlorideHCID 70072107HCID 70072107, 화합물

생성물 1

HCID 22850667HCID 22850667, 화합물수율 37.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
25 °C

실험 절차

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]).

후처리

  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

출처 및 근거

ORD 기록
ord-4d8ef0719f034fc58c6de681e1b5c720
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292726

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