Sodium t-butoxide → 5-[4-(2-Azepan-1-yl-ethoxy)-phenyl]-9-fluoro-5H-6-oxa-chrysen-2-ol

HRID 1513964ノート

反応式

HRID 1513964 の反応式
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([OH:37])[C:18]3[C:27]([C:28]4[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=4F)=[CH:26][CH:25]=[C:24]4[C:19]=3[CH:20]=[CH:21][C:22]([OH:36])=[CH:23]4)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)([O-])C.[Na+]>CN(C=O)C.O>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[O:37][C:29]4[C:28](=[CH:33][C:32]([F:34])=[CH:31][CH:30]=4)[C:27]4[C:18]3=[C:19]3[C:24](=[CH:25][CH:26]=4)[CH:23]=[C:22]([OH:36])[CH:21]=[CH:20]3)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 23676156Sodium t-butoxideHCID 670045865-{[4-(2-Azepan-1-yl-ethoxy)-phenyl]-hydroxymethyl}-6-(2,5-difluorophenyl)-naphthalen-2-ol

生成物 1

HCID 575525185-[4-(2-Azepan-1-yl-ethoxy)-phenyl]-9-fluoro-5H-6-oxa-chrysen-2-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Dissolve 5-{[4-(2-azepan-1-yl-ethoxy)-phenyl]-hydroxymethyl}-6-(2,5-difluorophenyl)-naphthalen-2-ol (770 mg, 1.54 mmol) in 20 mL dry DMF and add sodium t-butoxide (1.18 g, 12.32 mmol). Heat the mixture to 50° C. for two hours. Dilute with water and extract multiple times with methylene chloride. Dry the organic layer and purify on a silica gel column eluting with a 0-10% methanol/methylene chloride gradient. The yield is 370 mg (50%): 1H-NMR (CDCl3, 300 MHz) δ7.76 (dd, J=12.6, 8.4 Hz, 2H); 7.58 (d, J=9.0 Hz, 1H); 7.43-7.40 (m, 1H); 7.15 (d, J=2.4 Hz, 1H); 7.05-7.01 (m, 3H); 6.89 (s, 1H); 6.83-6.80 (m, 2H); 6.66-6.63 (m, 2H); 4.00-3.98 (m, 2H); 2.92-2.92 (m, 2H); 2.78-2.78 (m, 4H); 1.66-1.59 (m, 8H). The racemic compound is purified using chiral chromatography (conditions P). The two isomers eluted with retention times of 9.9 and 13.5 minutes.

後処理

  1. extractionextract multiple times with methylene chloride
  2. customDry the organic layer
  3. custompurify on a silica gel column
  4. washeluting with a 0-10% methanol/methylene chloride gradient
  5. customThe racemic compound is purified
  6. washThe two isomers eluted with retention times of 9.9 and 13.5 minutes

出典と根拠

ORDレコード
ord-b6933370dfe44e7fbaf6f0af0261ba80
出典データセット
uspto-grants-2012_07
特許番号
US08217032B2

反応ノート

読み込み中…