Ammonium Chloride → (S)-t-Butyl 2-(2-(2-((tert-butyldiphenylsilyl)oxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate

HRID 710042

反応式

HRID 710042 の反応式
[NH:1]([C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4])[NH2:2].[Si:17]([O:34][CH2:35][C:36](O)=[O:37])([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-]>O.C(Cl)(Cl)Cl>[Si:17]([O:34][CH2:35][C:36]([NH:2][NH:1][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4])=[O:37])([C:30]([CH3:32])([CH3:33])[CH3:31])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10014050tert-Butyl (2S)-2-(hydrazinecarbonyl)pyrrolidine-1-carboxylateHCID 111415642-((tert-Butyldiphenylsilyl)oxy)acetic acid

生成物 1

HCID 86706754(S)-t-Butyl 2-(2-(2-((tert-butyldiphenylsilyl)oxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate収率 61.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

A mixture of CHCl3 (100 mL) with (S)-t-butyl 2-(hydrazinecarbonyl)pyrrolidine-1-carboxylate (4.791 g), 2-((t-butyldiphenylsilyl)oxy)acetic acid (6.28 g), WSC.HCl (4.371 g) and HOBt.H2O (3.081 g) was stirred at room temperature for 15 hours. To the reaction mixture, a saturated aqueous solution of NH4Cl (500 mL) was added, followed by extraction with AcOEt (500 mL). The organic layer was washed successively with saturated aqueous sodium bicarbonate (500 mL) and brine (500 mL), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (6.42 g, colorless amorphous.)

後処理

  1. extractionfollowed by extraction with AcOEt (500 mL)
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate (500 mL) and brine (500 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas further purified by silica gel chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-e8a1dea0fe524084abffffd8048bbc51
出典データセット
uspto-grants-2015_11
特許番号
US09181229B2

関連ノート

読み込み中…