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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → Tert-butyl 1-(isopropoxycarbonyl)-4-oxo-3-o-tolylpentylcarbamate

HRID 706382
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HRID 706382 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16]OS(C)(=O)=O)[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([CH3:32])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][C:29](=[O:31])[CH3:30].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CS(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16][CH:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH3:32])[C:29](=[O:31])[CH3:30])[C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27341091-(2-Methylphenyl)propan-2-oneHCID 89815000isopropyl N-(tert-butoxycarbonyl)-O-(methylsulfonyl)serinate

생성물 1

HCID 89814785Tert-butyl 1-(isopropoxycarbonyl)-4-oxo-3-o-tolylpentylcarbamate수율 65.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 2 (181.2 g, 0.557 mol) in THF (1 L) was added TEA (84.6 g, 0.836 mol) in portions at 15-20° C. The mixture was stirred for 30 h. After the reaction was complete, the solution was concentrated to give crude 7. To a solution of 35 (82.5 g, 0.557 mol) and Cs2CO3 (91 g, 0.279 mol) in DMSO (1 L) was added slowly crude 7 in DMSO (500 mL) over 30 min at 15-20° C. The mixture was stirred for 1 h. After the reaction was complete, the mixture was partitioned with water and MTBE (5 L), and extracted with MTBE twice. The combined organic layer was dried over Na2SO4 and concentrated. The crude residual was further purified by flash chromatography on silica gel (5-10% EtOAc/PE) to give 36 (138 g, 65% yield).

후처리

  1. concentrationthe solution was concentrated
  2. customto give crude 7
  3. stirringThe mixture was stirred for 1 h
  4. customthe mixture was partitioned with water and MTBE (5 L)
  5. extractionextracted with MTBE twice
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude residual was further purified by flash chromatography on silica gel (5-10% EtOAc/PE)

출처 및 근거

ORD 기록
ord-1e1c02338f0f4433b4880d4b3b6b275f
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09174989B2

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