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Hydrochloric Acid → benzyl((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate

HRID 2079430
ノート
印刷プレビュー

反応式

HRID 2079430 の反応式
C(O[C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9]1)=O)(C)(C)C.Cl.ClC1[C:36]2[C:31](=[CH:32][C:33]([CH3:37])=[CH:34][CH:35]=2)[N:30]=[C:29]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[OH:44])[N:28]=1.C(N(CC)CC)C>O1CCOCC1.C(Cl)Cl>[OH:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[C:29]1[N:28]=[C:6]([N:8]2[CH2:12][CH2:11][C@@H:10]([CH2:13][NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:9]2)[C:36]2[C:31](=[CH:32][C:33]([CH3:37])=[CH:34][CH:35]=2)[N:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 59254364(S)-tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)pyrrolidine-1-carboxylateHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

生成物 1

HCID 136121473benzyl((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate収率 68%

試薬・触媒・溶媒

2
HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of benzyl ((S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylcarbamate (0.20 g, 0.60 mmol) and 4 M HCl in dioxane (10 mL) was stirred for 3 h at room temperature. After evaporating the solvent under reduced pressure, the solid was triturated with Et2O, dried under vacuum, and taken up in CH2Cl2 (10 mL). 2-(4-Chloro-7-methylquinazolin-2-yl)phenol (0.16 g, 0.60 mmol) was added to this solution, followed by the addition of triethylamine (0.25 mL, 1.8 mmol). The reaction mixture was stirred at room temperature overnight, then diluted with CH2Cl2 and washed with water. The combined organic layers were dried over Na2SO4, filtered, and concentrated. Purification via silica gel chromatography using 0-40% EtOAc in hexanes gave benzyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate as a colorless oil (0.19 g, 68% yield). LC/MS: m/z 469.1 (M+H)+ at 2.58 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

後処理

  1. customAfter evaporating the solvent under reduced pressure
  2. customthe solid was triturated with Et2O
  3. customdried under vacuum
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. washwashed with water
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification via silica gel chromatography

出典と根拠

ORDレコード
ord-37600f880ff64660ba5f51f993b6188d
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07928107B2

反応ノート

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