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Lithium Hydroxide → 2-Tert-butoxy-2-[4-(2,4-dimethylphenyl)-7-[1-(2-hydroxyethyl)triazol-4-yl]-2-methyl-1-oxo-3-isoquinolyl]acetic acid

HRID 572533
ノート
印刷プレビュー

反応式

HRID 572533 の反応式
[C:1]([O:5][CH:6]([C:11]1[N:12]([CH3:32])[C:13](=[O:31])[C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])=[CH:18][CH:17]=[C:16]([C:29]#[CH:30])[CH:15]=2)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].C([O:36][CH2:37][CH2:38][N:39]=[N+:40]=[N-:41])(=O)C.O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[OH-].[Li+]>C(O)C.O.C(OCC)(=O)C.CO.O1CCCC1.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:4][C:1]([O:5][CH:6]([C:11]1[N:12]([CH3:32])[C:13](=[O:31])[C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])=[CH:18][CH:17]=[C:16]([C:29]1[N:41]=[N:40][N:39]([CH2:38][CH2:37][OH:36])[CH:30]=1)[CH:15]=2)[C:7]([OH:9])=[O:8])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

11

反応物 4

HCID 3939Lithium HydroxideHCID 120185192-Azidoethyl acetateHCID 54670067L-Ascorbic AcidHCID 86700725Methyl 2-(tert-butoxy)-2-(4-(2,4-dimethylphenyl)-7-ethynyl-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate

生成物 1

HCID 715962962-Tert-butoxy-2-[4-(2,4-dimethylphenyl)-7-[1-(2-hydroxyethyl)triazol-4-yl]-2-methyl-1-oxo-3-isoquinolyl]acetic acid

試薬・触媒・溶媒 6

HCID 61499Cupric sulfate monohydrate触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of methyl 2-(tert-butoxy)-2-(4-(2,4-dimethylphenyl)-7-ethynyl-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate (26.0 mg, 0.060 mmol), 2-azidoethyl acetate (10.11 mg, 0.078 mmol), ascorbic acid (2.123 mg, 0.012 mmol) and copper sulfate monohydrate (1.923 mg, 0.012 mmol) in Ethanol (1.2 mL) and Water (0.2 mL) was irradiated in the microwave at 120° C. for 10 minutes. The mixture was diluted with ethyl acetate, then washed with saturated sodium bicarbonate and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The resulting crude residue in methanol (1.0 mL), tetrahydrofuran (THF) (1.0 mL) and water (0.2 mL) was treated with lithium hydroxide (28.8 mg, 1.205 mmol) and then heated to 60° C. for 90 minutes. The mixture was concentrated to dryness, water was added and the mixture was adjusted to pH 3-4 with 1N hydrochloric acid. The mixture was extracted with ethyl acetate; the extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by reverse phase chromatography to afford the desired product as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) (atropisomers) δ=8.75-8.54 (m, 1 H), 8.14 (br. s., 2 H), 7.43 (d, J=7.6 Hz, 1 H), 7.15 (d, J=14.6 Hz, 2 H), 7.04-6.85 (m, 1 H), 5.44-5.15 (m, 1 H), 4.56 (m, 2 H), 4.14 (m, 2 H), 3.83-3.64 (m, 3 H), 2.43 (s, 3 H), 2.15-1.83 (m, 3 H), 1.29-0.97 (m, 9 H); LC/MS (m/z) ES+=505 (M+1).

後処理

  1. customwas irradiated in the microwave at 120° C. for 10 minutes
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationThe mixture was concentrated to dryness, water
  7. additionwas added
  8. extractionThe mixture was extracted with ethyl acetate
  9. washthe extracts were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was purified by reverse phase chromatography

出典と根拠

ORDレコード
ord-307a6aa1080f4d0ea4725fce8f491eae
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09029391B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート