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Ammonium Chloride → (S)-t-Butyl 2-(4-((tert-butyldiphenylsilyl)oxy)but-2-ynoyl)pyrrolidine-1-carboxylate

HRID 710033
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HRID 710033 반응식
[Li]CCCC.[C:6]([Si:10]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:11][CH2:12][C:13]#[CH:14])([CH3:9])([CH3:8])[CH3:7].CON(C)[C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:31].[NH4+].[Cl-]>C1COCC1>[Si:10]([O:11][CH2:12][C:13]#[C:14][C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:31])([C:6]([CH3:9])([CH3:7])[CH3:8])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 610226Silane, (1,1-dimethylethyl)diphenyl(2-propynyloxy)-HCID 6882981,1-Dimethylethyl (2S)-2-[(methoxymethylamino)carbonyl]-1-pyrrolidinecarboxylateHCID 178418339Butyllithium

생성물 1

HCID 86706745(S)-t-Butyl 2-(4-((tert-butyldiphenylsilyl)oxy)but-2-ynoyl)pyrrolidine-1-carboxylate수율 56.2%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매2회

실험 절차

In an argon atmosphere, n-BuLi (10.3 mL, 2.64 N hexane solution) was added dropwise to a solution of t-butyldiphenyl(prop-2-yn-1-yloxy)silane (8.576 g) in THF (200 mL) at −78° C. over 10 minutes, and after stirring at room temperature for 50 minutes, the reaction mixture was added dropwise to a solution of (S)-t-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (5.01 g) in THF (200 mL) through a cannula and temperature was raised to room temperature over an hour. The reaction mixture was added to a saturated aqueous solution of NH4Cl (500 mL) and, after extraction with AcOEt, the organic layer was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (5.36 g, colorless oil.)

후처리

  1. temperaturewas raised to room temperature over an hour
  2. extractionafter extraction with AcOEt
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-2a5341d7992c42738b741facc0a034e5
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181229B2

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