Dimethylacetamide → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-{4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl}valerate

HRID 1912097노트

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HRID 1912097 반응식
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30]1[C:34](I)=[C:33]([CH:36]2[CH2:39][CH:38]([CH2:40][CH:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH2:37]2)[O:32][N:31]=1)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:46]1(B2OC(C)(C)C(C)(C)O2)[CH2:48][CH2:47]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C(=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30]1[C:34]([CH:46]2[CH2:48][CH2:47]2)=[C:33]([CH:36]2[CH2:39][CH:38]([CH2:40][CH:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH2:37]2)[O:32][N:31]=1)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71127336tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-{5-[3-(2-ethylbutyl)cyclobutyl]-4-iodoisoxazol-3-yl}valerate

생성물 1

HCID 71114789tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-{4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl}valerate수율 65.2%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-{5-[3-(2-ethylbutyl)cyclobutyl]-4-iodoisoxazol-3-yl}valerate (4.96 g), 2-cyclopropyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.68 g), tripotassium phosphate (5.66 g), PdCl2(PPh3)2 (468 mg) and N,N-dimethylacetamide (50 mL) were mixed. The mixture was stirred at 80° C. for 5 hr. To the reaction mixture were added ethyl acetate (50 mL) and Celite at RT, and the mixture was filtered. The collected solid was washed with ethyl acetate (50 mL×2). The filtrate was washed with water/brine=1/1 (100 mL×2) and brine (50 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/50→1/40→1/30→1/20) to give the title compound (2.86 g).

후처리

  1. filtrationthe mixture was filtered
  2. washThe collected solid was washed with ethyl acetate (50 mL×2)
  3. washThe filtrate was washed with water/brine=1/1 (100 mL×2) and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/50→1/40→1/30→1/20)

출처 및 근거

ORD 기록
ord-d091e1c03ff343e4a1fee1fbf3293487
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604069B2

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