Water → HCID 178474735, 화합물

HRID 579586

반응식

HRID 579586 반응식
[C:1]([NH:4][C:5]([C@@H:17]1[CH2:20][C@H:19]([N:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18]1)([CH2:13][CH2:14][CH:15]=[CH2:16])[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[CH3:36][C:37]1([CH3:44])[C:41]([CH3:43])([CH3:42])[O:40][BH:39][O:38]1.O>ClCCl.[Ir+].ClC1CCC=CCCC=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([NH:4][C:5]([C@@H:17]1[CH2:18][C@H:19]([N:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:20]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:39]1[O:40][C:41]([CH3:43])([CH3:42])[C:37]([CH3:44])([CH3:36])[O:38]1)[C:6]([NH:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 962WaterHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 178446405HCID 178446405, 화합물

생성물 1

HCID 178474735HCID 178474735, 화합물수율 74.6%

시약·촉매·용매 3

HCID 742671,2-Bis(diphenylphosphino)ethane촉매HCID 178478077HCID 178478077, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

After stirring for 30 min, a solution of cis-tert-butyl 3-(2-acetamido-1-(tert-butylamino)-1-oxohex-5-en-2-yl)cyclobutyl(benzyl)carbamate (5.34 g, 10.5 mmol), chloro-1,5-cyclooctadiene iridium(I) dimer (212 mg, 0.32 mmol, 3 mol %) and 1,2-bis(diphenylphosphino)ethane (252 mg, 0.63 mmol, 6 mol %) in dichloromethane (50 mL) was cooled to 0° C. and carefully treated with 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.1 mL, 21.1 mmol, 2 eq) over 5 min. After slowly warming to room temperature and stirring overnight, the reaction was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (silica gel, 10-40% ethyl acetate in heptane) gave cis-tert-butyl 3-(2-acetamido-1-(tert-butylamino)-1-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-2-yl)cyclobutyl(benzyl)carbamate (4.8 g, 7.83 mmol, 74%). ESI MS found for C34H56BN3O6 m/z [614.2 (M+1), 636.2 (M+23)].

후처리

  1. stirringstirring overnight
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, 10-40% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-145b60898c134376ae3964236b0ea64a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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