1-Hydroxybenzotriazole → 9-[Oxo-(3,4,5-trimethoxyphenyl)-acetyl]-3-(4-phenyl-butyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione

HRID 987088ノート

反応式

HRID 987088 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:18](=[O:19])[CH:17]3[NH:20][CH:13]([CH2:14][CH2:15][CH2:16]3)[C:12]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:23]1[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[C:26]([O:33][CH3:34])=[CH:25][CH:24]1[CH2:35][C:36]([OH:38])=O.C1C=CC2N([OH:48])N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[O:48]=[C:35]([C:24]1[CH:25]=[C:26]([O:33][CH3:34])[C:27]([O:31][CH3:32])=[C:28]([O:29][CH3:30])[CH:23]=1)[C:36]([N:20]1[CH:17]2[CH2:16][CH2:15][CH2:14][CH:13]1[C:12](=[O:21])[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:18]2=[O:19])=[O:38]

参加物

6

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 229879053-(4-Phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione2 回HCID 696972782-Oxo-3,4,5-trimethoxyphenylacetic acid

生成物 1

HCID 229879039-[Oxo-(3,4,5-trimethoxyphenyl)-acetyl]-3-(4-phenyl-butyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione収率 34%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

3-(4-Phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione (Compound 14, 0.42 g, 1.47 mmol) and 2-oxo-3,4,5-trimethoxyphenylacetic acid (0.35 g, 1.47 mmol) were dissolved in CH2Cl2 (5 mL), and the solution was cooled to 0° C. HOBt (0.21 g, 1.54 mmol) was added, followed by EDC.HCl (0.30 g, 1.54 mmol) and TEA (0.15 g, 1.47 mmol). The reaction was allowed to reach room temperature and stirred for 5 hours. The volatiles were removed using a high-vacuum rotary evaporator. The residue was dissolved in EtOAc and washed with 10% citric acid solution (10 mL), followed by water (10 mL), saturated NaHCO3 (10 mL), and brine (10 mL). The combined organic layers were dried over Na2SO4 and were concentrated. Flash chromatographic purification of the residue (30% EtOAc/hexanes) gave Compound 15 as a pale-yellow solid (0.25 g, 34%, one isomer). mp=101-103° C.; Rf=0.32 (50% EtOAc/hexanes); IR: 2939, 2866, 1739, 1682, 1651, 1582, 1503, 1454, 1416, 1361, 1337, 1243, 1167, 1126, 1067, 991, 914, 862 cm−1; 1H NMR (major rotamer): δ 1.56-1.64 (m, 5H), 1.93-2.01 (m, 5H), 2.61-2.66 (m, 2H), 3.80-3.85 (m, 2H), 3.95 (s, 9H), 4.51 (brs, 1H), 5.46 (brs, 1H),7.14-7.29 (m, 7H); HRMS (M+H+): expected 509.2288, observed 509.2275; EA: calculated, C (66.13), H (6.34), N (5.51); found, C (66.00, H (6.37), N (5.50).

後処理

  1. customto reach room temperature
  2. customThe volatiles were removed
  3. customa high-vacuum rotary evaporator
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 10% citric acid solution (10 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationwere concentrated
  8. customFlash chromatographic purification of the residue (30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-1cea540ebd574f6fae8eefd4f36949dd
出典データセット
uspto-grants-2003_10
特許番号
US06630472B1

反応ノート

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