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Sodium hydride → [3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid 2-(4-bromo-2-ethyl-phenyl)-ethyl ester

HRID 735617
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HRID 735617 반응식
[H-].[Na+].C1([O:9][C:10](=[O:34])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[C:14]([CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:26])[CH:13]=2)C=CC=CC=1.[Br:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43]O)=[C:38]([CH2:45][CH3:46])[CH:37]=1>C1COCC1>[Br:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][O:9][C:10](=[O:34])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[C:14]([CH2:24][N:25]([C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[CH3:26])[CH:13]=2)=[C:38]([CH2:45][CH3:46])[CH:37]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 578427842-(4-Bromo-2-ethylphenyl)ethanolHCID 57842905[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid phenyl ester

생성물 1

HCID 57842899[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid 2-(4-bromo-2-ethyl-phenyl)-ethyl ester수율 92%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

NaH (190 mg, 4.7 mmol) was added in one portion to a solution of 16G (547 mg, 1.2 mmol) and 36B (1000 mg, 4.4 mmol) in THF (20 mL) at −40° C. The reaction was warmed slowly to ambient temperature over 2 h and stirred for 15 h. The reaction was quenched with saturated citric acid and diluted with EtOAc. The mixture washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to afford 43A (650 mg, 92%) as a yellow solid. MS (ESI) m/z 597.1/599.1 (M+H)+.

후처리

  1. customThe reaction was quenched with saturated citric acid
  2. additiondiluted with EtOAc
  3. washThe mixture washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-9ab51c9227fd4cea910b3c912a424db7
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592331B2

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