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Ethyldiphenylphosphine → tert-butyl 4-(tert-butylcarbamoyl)-4-(N-methylacetamido)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octylcarbamate

HRID 579541
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HRID 579541 반응식
C1(P(CC)C2C=CC=CC=2)C=CC=CC=1.[CH3:16][C:17]1([CH3:24])[C:21]([CH3:23])([CH3:22])[O:20][BH:19][O:18]1.[C:25]([NH:29][C:30]([C:32]([N:48]([CH3:52])[C:49](=[O:51])[CH3:50])([CH2:44][CH2:45][CH:46]=[CH2:47])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([NH:29][C:30]([C:32]([N:48]([CH3:52])[C:49](=[O:51])[CH3:50])([CH2:44][CH2:45][CH2:46][CH2:47][B:19]1[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:24])([CH3:16])[O:18]1)[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:31])([CH3:26])([CH3:27])[CH3:28]
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참가 물질

5

반응물 3

HCID 69082EthyldiphenylphosphineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 86663727tert-butyl 4-(tert-butylcarbamoyl)-4-(N-methylacetamido)oct-7-enylcarbamate

생성물 1

HCID 66833610tert-butyl 4-(tert-butylcarbamoyl)-4-(N-methylacetamido)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octylcarbamate수율 90.1%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
3회

실험 절차

While under an atmosphere of argon, a solution of bis(1,5-dicyclooctadiene)diiridium(I)dichloride (6 mg; 0.009 mmol) and diphenylphosphinoethane (7 mg, 0.018 mmol) in dichloromethane (1 mL) was cooled to 0° C. and treated with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.174 mL, 1.2 mmol). After stirring for 30 min, a solution of tert-butyl 4-(tert-butylcarbamoyl)-4-(N-methylacetamido)oct-7-enylcarbamate (120 mg, 0.3 mmol) in dichloromethane (4 mL) was added and the solution was stirred an additional 16 h. Dichloromethane (10 mL) was added, and the solution was washed successively with water and sat'd aq sodium chloride, dried over MgSO4, filtered and concentrated. Purification by column chromatography (3% methanol in dichloromethane) gave tert-butyl 4-(tert-butylcarbamoyl)-4-(N-methylacetamido)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octylcarbamate (142 mg, 90%). ESI MS found for C27H52BN3O6 m/z [548.7 (M+Na+), 526.7 (M+1), 570.8 (M+HCOO−), 524.6 (M−1)].

후처리

  1. stirringthe solution was stirred an additional 16 h
  2. washthe solution was washed successively with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (3% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-0b13197b573e4b33a04650618c7090b8
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040703B2

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