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Diisopropylamine → tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(5-tributylstannyl-1,3-thiazol-2-yl)carbamate

HRID 2353700
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HRID 2353700 반응식
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]([O:17][C:18]([N:20]([C:28]1[S:29][CH:30]=[CH:31][N:32]=1)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])([CH3:16])[CH3:15].[CH2:33]([Sn:37](Cl)([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH3:36]>C1COCC1>[CH3:26][C:23]([O:22][C:21]([N:20]([C:28]1[S:29][C:30]([Sn:37]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:31][N:32]=1)[C:18](=[O:19])[O:17][C:14]([CH3:13])([CH3:15])[CH3:16])=[O:27])([CH3:24])[CH3:25]
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참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 15096Tributyltin ChlorideHCID 59379867tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(1,3-thiazol-2-yl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 59380135tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(5-tributylstannyl-1,3-thiazol-2-yl)carbamate

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

n-Butyl lithium (1.6M in hexanes, 30 mL, 0.48 mol), was added to diisopropylamine (6.7 mL, 0.48 mol) in THF (480 mL) at 0° C. The mixture was stirred at 0° C. for 30 mins then cooled to −78° C. tert-Butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(1,3-thiazol-2-yl)carbamate (12 g, 0.05 mol) was added and solution stirred for 30 minutes. Tributyltin chloride (16.3 mL) was added and solution stirred for 30 minutes before allowing to warm to RT. The reaction was quenched with a saturated aqueous solution of ammonium chloride (20 mL) and the product extracted with ethyl acetate. The organics were dried over sodium sulphate, concentrated in vacuo and chromatographed on silica, eluting with 5-15% ethyl acetate in hexane, to give the desired material as a clear oil (9 g).

후처리

  1. additionwas added
  2. stirringsolution stirred for 30 minutes
  3. stirringsolution stirred for 30 minutes
  4. temperatureto warm to RT
  5. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride (20 mL)
  6. extractionthe product extracted with ethyl acetate
  7. dry with materialThe organics were dried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica
  10. washeluting with 5-15% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ed4b38cce4964a0488aa2d26ba225652
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07750003B2

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