Ethyl chloroformate → 1,3-Dimethyl-4-pyrrolidinoacetyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

HRID 1902490

반응식

HRID 1902490 반응식
ClC(OCC)=O.[N:7]1([CH2:12][C:13]([OH:15])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:16][N:17]1[C:26]2[C:25](=[O:27])[NH:24][C:23]3[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=3[NH:21][C:20]=2[C:19]([CH3:32])=[CH:18]1.[OH-].[Na+]>O1CCCC1>[CH3:16][N:17]1[C:26]2[C:25](=[O:27])[NH:24][C:23]3[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=3[N:21]([C:13](=[O:15])[CH2:12][N:7]3[CH2:8][CH2:9][CH2:10][CH2:11]3)[C:20]=2[C:19]([CH3:32])=[CH:18]1

참가 물질

6

반응물 4

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 414564Pyrrolidin-1-ylacetic acidHCID 189759801,3-Dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

생성물 1

HCID 205154481,3-Dimethyl-4-pyrrolidinoacetyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one수율 62.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

1.1 g of ethyl chloroformate are added dropwise at 0° C. to a suspension of 1.29 g of pyrrolidin-1-ylacetic acid in 20 ml of tetrahydrofuran. 2.28 g of 1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one are added to the obtained suspension. The mixture is stirred 1 hour at 0° C. and a further 4 hours at room temperature. It is then poured onto 160 ml of 2 N sodium hydroxide solution and extracted with toluene. The organic phase is concentrated to dryness. The residue is chromatographed over a silica gel column by means of a mixture of dioxane/methanol (1:1) to yield 2.1 g of the title compound of m.p. 210° to 212° C. (from isopropanol).

후처리

  1. extractionextracted with toluene
  2. concentrationThe organic phase is concentrated to dryness
  3. customThe residue is chromatographed over a silica gel column by means of a mixture of dioxane/methanol (1:1)

출처 및 근거

ORD 기록
ord-bdcd95f8e4ee4586a6e00e95cb8c3b04
출처 데이터셋
uspto-grants-1982_12
특허 번호
US04363816

연결된 노트

불러오는 중…