Water → HCID 53704459, 화합물

HRID 357325노트

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HRID 357325 반응식
[CH2:1]([N:5]([CH3:38])[C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[C:17]([C:29]1[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=1)[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1)[CH2:19][CH3:20])[CH2:2][CH2:3][CH3:4].[Br-].[Br-].[Br-].B.O>C(Cl)Cl>[CH2:1]([N:5]([CH3:38])[C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[C:18]([C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)[CH2:19][CH3:20])[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 54103883HCID 54103883, 화합물HCID 178419136HCID 178419136, 화합물

생성물 1

HCID 53704459HCID 53704459, 화합물수율 31.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To the above dimethoxy amide 4 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0M borane tribromide (675 μl). The solution was stirred for 1 hour, then poured into water and extracted with ether (3×). 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, under 0.063 mm, 30 g). Elution with 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 5 with x=10) (34 mg, 31%), colorless oil, IR νmax (neat) 3300, 1600 cm-1 ; UV γmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J=7.3 Hz, --C2CHH3), 0.96 (3H, t, J=7.3 Hz, N(CH2)3 CH3), 2.05-2.20 (4H, m, CH2 --C=C--C2 --), 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 (8H, m, H--Ar) ppm; MS m/e=493 (M+). ##STR74##

후처리

  1. extractionextracted with ether (3×)
  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, under 0.063 mm, 30 g)
  6. washElution
  7. additionwith mixture of hexane-ethyl acetate (4:1 v/v)

출처 및 근거

ORD 기록
ord-bd9e55800b2347fe8bea0b58d1fa2c3c
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840735

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