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3-Cyclopentylpropionyl chloride → (2S)-2-tert-butoxy-2-(2-(3-cyclopentylpropanamido)-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

HRID 1468751
ノート
印刷プレビュー

反応式

HRID 1468751 の反応式
[NH2:1][C:2]1[CH:32]=[C:5]2[N:6]=[C:7]([CH3:31])[C:8]([C@H:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])=[C:9]([C:10]3[C:11]([CH3:21])=[C:12]4[C:17](=[C:18]([F:20])[CH:19]=3)[O:16][CH2:15][CH2:14][CH2:13]4)[N:4]2[N:3]=1.NC1C=C2N=C(C)C(C(OC(C)(C)C)C(O)=O)=C(C3[C:43]([CH3:53])=[C:44]4[C:49](=[C:50](F)C=3)[O:48][CH2:47][CH2:46][CH2:45]4)N2N=1.C1(CCC(Cl)=O)CCCC1.CCN(C(C)C)C(C)C>C1COCC1>[C:27]([O:26][C@@H:22]([C:8]1[C:7]([CH3:31])=[N:6][C:5]2[N:4]([N:3]=[C:2]([NH:1][C:47](=[O:48])[CH2:46][CH2:45][CH:44]3[CH2:43][CH2:53][CH2:50][CH2:49]3)[CH:32]=2)[C:9]=1[C:10]1[C:11]([CH3:21])=[C:12]2[C:17](=[C:18]([F:20])[CH:19]=1)[O:16][CH2:15][CH2:14][CH2:13]2)[C:23]([OH:25])=[O:24])([CH3:28])([CH3:29])[CH3:30]
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 660393-Cyclopentylpropionyl chlorideHCID 81531DiisopropylethylamineHCID 71730302(2S)-2-(2-amino-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetic acidHCID 781617522-(2-Amino-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetic acid

生成物 1

HCID 71730303
(2S)-2-tert-butoxy-2-(2-(3-cyclopentylpropanamido)-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid
収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2S)-2-(2-amino-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetic acid (22 mg, 0.050 mmol), 3-cyclopentylpropanoyl chloride (8.79 mg, 0.055 mmol), Hunig's Base (0.026 mL, 0.15 mmol) in THF (2 mL) was stirred at rt for 16 h. It was then concentrated in vacuo and purified by prep HPLC (TFA/MeOH), the desired fractions were combined and adjusted to pH=6 using a few drops of 1N NaOH. The residue was then acidified to pH=4 using a few drops of 1N HCl. This solution was extracted with EtOAc. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to obtain (10 mg, 35%) of (2S)-2-tert-butoxy-2-(2-(3-cyclopentylpropanamido)-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid as white solid.

後処理

  1. concentrationIt was then concentrated in vacuo
  2. custompurified by prep HPLC (TFA/MeOH)
  3. extractionThis solution was extracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-efb6ad2c75994449a8ff2dd6858754ee
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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