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Trityl chloride → (1S,4R)-methyl 4-(tritylamino)cyclopent-2-enecarboxylate

HRID 1427327
ノート
印刷プレビュー

反応式

HRID 1427327 の反応式
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@@H:9]([NH2:11])[CH:8]=[CH:7]1)=[O:5].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[C:18]([NH:11][C@@H:9]1[CH2:10][C@H:6]([C:4]([O:3][CH3:2])=[O:5])[CH:7]=[CH:8]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
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

5

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 60152708(1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate hydrochloride

生成物 1

HCID 78358250(1S,4R)-methyl 4-(tritylamino)cyclopent-2-enecarboxylate収率 105.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Methyl-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride (5.50 g) was suspended in methylene chloride (60 mL), to which triphenylmethyl chloride (9.06 g, 0.0325 mol) was added. The mixture was then cooled to 0° C. Triethylamine (10.8 mL, 0.0774 mol) was then added dropwise keeping the temperature less than 10° C. Upon completion of addition, the mixture was allowed to warm to 20-25° C. The mixture was left to stir at 20-25° C. for 17 hours. The mixture was then washed with water (3×50 mL). The aqueous washes were combined and extracted with DCM (50 mL). The organics were combined and washed with brine (20 mL) and the solvent was removed under reduced pressure to afford the title compound as a brown oil (12.5 g) which was used without further purification. 1H NMR (300 MHz, CDCl3, δ): 7.58 (m, 6H), 7.27 (m, 6H), 7.18 (m, 3H), 5.57 (m, 1H), 4.93 (m, 1H), 3.76 (m, 1H), 3.65 (s, 3H), 3.18 (m, 1H), 2.11 (m, 1H), 1.90 (m, 1H) and 1.53 (m, 1H).

後処理

  1. additionwas added
  2. customthe temperature less than 10° C
  3. additionUpon completion of addition
  4. temperatureto warm to 20-25° C
  5. waitThe mixture was left
  6. washThe mixture was then washed with water (3×50 mL)
  7. extractionextracted with DCM (50 mL)
  8. washwashed with brine (20 mL)
  9. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-04a818ab8fb248c3a579114a08304c4a
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933225B2

反応ノート

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