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Bromomethylcyclopropane → ((S)-1-cyclopropylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

HRID 1374552
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인쇄 미리보기

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HRID 1374552 반응식
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:32][CH:33]1[CH2:35][CH2:34]1>O1CCCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 81503BromomethylcyclopropaneHCID 2733832Lithium hexamethyldisilazaneHCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate

생성물 1

HCID 58595315((S)-1-cyclopropylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester수율 40%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-75 °C

실험 절차

To a solution of 0.6 g (2.2 mmol) (S)-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester in 10 ml of tetrahydrofuran at −75° C. 2.2 ml (2.2 mmol) of lithium bis(trimethylsilyl)amide solution (1M in tetrahydrofurane) was added. After stirring for 30 min at −75° C. the mixture was allowed to reach room temperature and 0.35 g (2.6 mmol) of bromomethyl-cyclopropane was added. The mixture was stirred for 2.5 hours at room temperature and concentrated in vacuo. The residue was distributed between 1M NaHSO4 solution and ethyl acetate. The combined organic layers were re-extracted with water and dried (MgSO4) to yield 0.285 g (40%) of ((S)-1-cyclopropylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester.

후처리

  1. customat −75° C
  2. customto reach room temperature
  3. stirringThe mixture was stirred for 2.5 hours at room temperature
  4. concentrationconcentrated in vacuo
  5. extractionThe combined organic layers were re-extracted with water
  6. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-71df74ed0e524c9788dac4ea43bb5d8d
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07166587B2

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