Nitrogen → {4-[2-(3,4,5-Trihydroxy-phenyl)-acetyl]piperazin-1-yl}-acetic acid ethyl ester

HRID 383599

반응식

HRID 383599 반응식
N#N.[CH2:3]([O:5][C:6](=[O:29])[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:28])[CH2:15][C:16]2[CH:21]=[C:20]([O:22]C)[C:19]([O:24]C)=[C:18]([O:26]C)[CH:17]=2)[CH2:10][CH2:9]1)[CH3:4].B(Br)(Br)Br.O>C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:29])[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:28])[CH2:15][C:16]2[CH:21]=[C:20]([OH:22])[C:19]([OH:24])=[C:18]([OH:26])[CH:17]=2)[CH2:10][CH2:9]1)[CH3:4]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 962WaterHCID 25134Boron tribromideHCID 59785709{4-[2-(3,4,5-Trimethoxy-phenyl)-acetyl]-piperazin-1-yl}-acetic acid ethyl ester

생성물 1

HCID 59819847{4-[2-(3,4,5-Trihydroxy-phenyl)-acetyl]piperazin-1-yl}-acetic acid ethyl ester수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve {4-[2-(3,4,5-Trimethoxy-phenyl)-acetyl]-piperazin-1-yl}-acetic acid ethyl ester (64) (99 mg, 0.26 mmol) in anhydrous DCM (6.0 mL), cool the solution to −78° C. and add dropwise a 1 M BBr3 solution in DCM (2.30 mL, 2.30=101). Stir the reaction mixture for 30 min at −78° C. and after slowly warming up for additional 4 h at −20° C. Add dropwise water and extract the mixture with EtOAc (3 times). Wash the combined organic layer with brine and dry it dry with Na2SO4. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain {4-[2-(3,4,5-Trihydroxy-phenyl)-acetyl]-piperazin-1-yl}-acetic acid ethyl ester (65) (34 mg, 40%) as a sticky brownish solid. 1H NMR (400 MHz, CD3OD): 1.35 (t, 3H, J=7.1 Hz); 3.14-3.24 (br.m, 2H); ca. 3.32 (br.m, 2H); 3.65 (s, 2H); 3.78-4.00 (br.m, 4H); 4.12 (s, 2H); 4.34 (q, 2H, J=7.1 Hz); 6.29 (s, 2H).

후처리

  1. custom(The following reaction
  2. temperatureafter slowly warming up for additional 4 h at −20° C
  3. extractionextract the mixture with EtOAc (3 times)
  4. washWash the combined organic layer with brine
  5. customdry it
  6. dry with materialdry with Na2SO4
  7. customPurify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95)

출처 및 근거

ORD 기록
ord-fc780e3d8f7e47399ef5f69de47faf8f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367677B2

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