Racemic (2'R,3R,4'S)-1'-(aminocarbonyl-methyl)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)-2,3-dihydro-2,6'-dioxo-spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane → racemic (2'R,3R,4'S)-1'-(aminocarbonyl-methyl)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728161ノート

反応式

HRID 1728161 の反応式
[NH2:1][C:2]([CH2:4][N:5]1[C:10](=[O:11])[CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:7]2([C:26]3[C:21](=[CH:22][C:23]([Br:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[CH:6]1[C:29](=[CH2:32])[CH2:30][CH3:31])=[O:3].COC([Si](C)(C)C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:1][C:2]([CH2:4][N:5]1[C:10](=[O:11])[CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:7]2([C:26]3[C:21](=[CH:22][C:23]([Br:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[CH:6]1[C:29](=[CH2:32])[CH2:30][CH3:31])=[O:3]

参加物

4

反応物 1

HCID 77580671Racemic (2'R,3R,4'S)-1'-(aminocarbonyl-methyl)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)-2,3-dihydro-2,6'-dioxo-spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

生成物 1

HCID 76567866racemic (2'R,3R,4'S)-1'-(aminocarbonyl-methyl)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione収率 25.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

Racemic (2′R,3R,4′S)-1′-(aminocarbonyl-methyl)-6-bromo-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)-2,3-dihydro-2,6′-dioxo-spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (350 mg) was dissolved in a solution of trifluoroacetic acid (5 mL) and dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 0.5 h. The reaction mixture was concentrated. The residue was redissolved in a mixture of methanol (3 ml) and DIPEA. The reaction tube was then placed into the cavity of a focused monomode microwave reactor and the contents of the flask were irradiated for 30 min at 120° C. The reaction mixture was concentrated and the residue was concentrated and the residue was purified by Prep-HPLC to obtain 70 mg product.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was redissolved in a mixture of methanol (3 ml) and DIPEA
  3. customThe reaction tube was then placed into the cavity of a focused monomode microwave reactor
  4. customthe contents of the flask were irradiated for 30 min at 120° C
  5. concentrationThe reaction mixture was concentrated
  6. concentrationthe residue was concentrated
  7. customthe residue was purified by Prep-HPLC

出典と根拠

ORDレコード
ord-d08f613dc01044ce978b6e90270ebaf7
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

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