Hexane → HCID 17932014, 화합물

HRID 2174323노트

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HRID 2174323 반응식
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH:12]([Br:16])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(=N)O[C:22]([CH3:25])([CH3:24])[CH3:23].CN(C)C(=O)C.CCCCCC>C(Cl)(Cl)Cl.C1CCCCC1.B(F)(F)F.CCOCC>[C:22]([O:14][C:13](=[O:15])[CH:12]([Br:16])[CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])([CH3:25])([CH3:24])[CH3:23]

참가 물질

8

반응물 4

HCID 8058HexaneHCID 31374DimethylacetamideHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21197492HCID 21197492, 화합물

생성물 1

HCID 17932014HCID 17932014, 화합물수율 79.1%

시약·촉매·용매 3

HCID 8000Boron trifluoride etherate촉매HCID 6212Chloroform용매HCID 8078Cyclohexane용매

실험 절차

To a solution of α-bromoglutaric acid-5-benzylester (See Example 18a(i)(a); 1.2 g, 4.0 mmol) in chloroform (Merck, 5 mL) a solution of tert-butyl 2,2,2-trichloroacetimidate (Fluka, 1.57 mL, 8.52 mmol) in cyclohexane (Merck, 5 mL) was added dropwise over 5 minutes. N,N-Dimethylacetamide (Fluka, 0.88 mL) was added followed by boron trifluoride ethyl etherate (Aldrich, 80 μL) as catalyst. The reaction mixture was stirred for 5 days at room temperature. Hexane was added and the organic phase washed with brine three times, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified using normal phase chromatography (Silica column (40 g), solvents: A=hexane, B=ethyl acetate, gradient: 10 to 35% B over 15 min, flow rate 40 mL/min, UV detection at 214 and 254 nm) affording 1.13 g (79%) of the pure product. Structure was verified by NMR

후처리

  1. washthe organic phase washed with brine three times
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product was purified
  5. waitA=hexane, B=ethyl acetate, gradient: 10 to 35% B over 15 min

출처 및 근거

ORD 기록
ord-05082266f0714dfaa634dbb968f0fe93
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061080B2

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