Water → HCID 53738029, 화합물

HRID 1081520노트

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HRID 1081520 반응식
[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1)[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1)[CH2:16][CH3:17].[Br-].[Br-].[Br-].B.O>C(Cl)Cl>[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[C:15]([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[CH2:16][CH3:17]

참가 물질

5

반응물 3

HCID 962WaterHCID 54079109N-methyl-12,13-Bis(4-methoxyphenyl)-11-pentadecenoic amideHCID 178419136HCID 178419136, 화합물

생성물 1

HCID 53738029HCID 53738029, 화합물수율 35.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To the above dimethoxy amide 15 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0 M borane tribromide (675 μl). The solution was stirred for 1 hour then poured into water and extracted with ether (3x). The organic solution was washed with water, dried on magnesium sulfate, and evaporated to dryness. The residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, unter 0.063 mm, 30 g). Elution with a mixture of hexane-ethyl acetate (4:1 v/v) gave N-butyl, N-methyl-12,13-Bis (4-hydroxyphenyl)-12-pentadecenoic amide ("EM-142", compound 16 with x=10) (34 mg, 31%), colorless oil, IR υmax (neat) 3300, 1600 cm-1 ; UV λmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J=7.3 Hz, --CH2CH3), 0.96 (3H, t,J=7.3 Hz, N (CH2)3CH3), 2.05-2.20 (4H, m, CH2 --C=C--CH2 --), 2.35 (2H, t,J=7.0 Hz, --CH2CON--), 2.97 and 3.00 (3H, s, --NCH3), 3.29 and 3.41 (2H, 2t, J=7.3 Hz --N--CH2 --), and 6.59-7.09 (8, m, H--Ar) ppm; MS m/e=493 (M+). ##STR23##

후처리

  1. extractionextracted with ether (3x)
  2. washThe organic solution was washed with water
  3. customdried on magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, unter 0.063 mm, 30 g)
  6. washElution
  7. additionwith a mixture of hexane-ethyl acetate (4:1 v/v)

출처 및 근거

ORD 기록
ord-25fec5e4f8c34a1b8717bdb3b749608e
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05585405

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