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Triethylamine → (2S)-ethyl 2-tert-butoxy-2-(7-(8-fluoro-5-methylchroman-6-yl)-5-methyl-2-((2-(trimethylsilyl)ethoxy)carbonylamino)pyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 1468748
ノート
印刷プレビュー

反応式

HRID 1468748 の反応式
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:36])=[N:14][C:15]2[N:16]([N:30]=[C:31](C(O)=O)[CH:32]=2)[C:17]=1[C:18]1[C:19]([CH3:29])=[C:20]2[C:25](=[C:26]([F:28])[CH:27]=1)[O:24][CH2:23][CH2:22][CH2:21]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])C=CC=CC=1.[CH3:54][Si:55]([CH3:60])([CH3:59])[CH2:56][CH2:57][OH:58].C([N:63]([CH2:66]C)CC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:36])=[N:14][C:15]2[N:16]([N:30]=[C:31]([NH:63][C:66]([O:58][CH2:57][CH2:56][Si:55]([CH3:60])([CH3:59])[CH3:54])=[O:44])[CH:32]=2)[C:17]=1[C:18]1[C:19]([CH3:29])=[C:20]2[C:25](=[C:26]([F:28])[CH:27]=1)[O:24][CH2:23][CH2:22][CH2:21]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:4])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 712583786-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid

生成物 1

HCID 86695369(2S)-ethyl 2-tert-butoxy-2-(7-(8-fluoro-5-methylchroman-6-yl)-5-methyl-2-((2-(trimethylsilyl)ethoxy)carbonylamino)pyrazolo[1,5-a]pyrimidin-6-yl)acetate
収率 70.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid (3.40 g, 5.79 mmol), diphenylphosphoryl azide (1.50 mL, 6.94 mmol), 2-(trimethylsilyl)ethanol (1.66 mL, 11.6 mmol), triethylamine (0.968 mL, 6.94 mmol) in toluene (100 mL) was refluxed for 16 h. It was then concentrated in vacuo. The residue was purified by biotage eluting with 20% EtOAc/hexane to isolate 2.5 g (70%) of (2S)-ethyl 2-tert-butoxy-2-(7-(8-fluoro-5-methylchroman-6-yl)-5-methyl-2-((2-(trimethylsilyl)ethoxy)carbonylamino)pyrazolo[1,5-a]pyrimidin-6-yl)acetate as off-white solid. 1H NMR (500 MHz, CDCl3) δ 7.25 (s, 1H), 6.89 (s, 1H), 6.87 (d, J=6.9 Hz, 1H), 4.90 (s, 1H), 4.34 (m, 2H), 4.30 (m, 2H), 4.13 (d, J=7.1 Hz, 2H), 2.84-2.63 (m, 5H), 2.18 (m, 2H), 1.84 (s, 3H), 1.20 (t, J=7.1 Hz, 3H), 1.17 (s, 9H), 1.05 (m, 2H), 0.07 (s, 9H). LCMS (M+H)=615.4.

後処理

  1. temperaturewas refluxed for 16 h
  2. concentrationIt was then concentrated in vacuo
  3. customThe residue was purified by biotage
  4. washeluting with 20% EtOAc/hexane

出典と根拠

ORDレコード
ord-6a6bbdbe4ccf487290101d27b1b67bce
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006235B2

反応ノート

読み込み中…

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