ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Acetonitrile → tert-butyl (2S,3R,5E)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]-2-(1-propyl)hex-5-enoate

HRID 1700984
ノート
印刷プレビュー

反応式

HRID 1700984 の反応式
[CH3:1][C:2]([CH3:34])([CH3:33])[C@H:3]([NH:15][C:16]([C@H:18]([CH2:30][CH:31]=[CH2:32])[C@H:19]([CH2:27][CH2:28][CH3:29])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])[C:4]([NH:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:5].[CH3:35][C:36]1[CH:37]=[C:38](Br)[CH:39]=[CH:40][C:41]=1[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(#N)C>CN(C)C=O>[CH3:34][C:2]([CH3:1])([CH3:33])[C@H:3]([NH:15][C:16]([C@H:18]([CH2:30]/[CH:31]=[CH:32]/[C:38]1[CH:39]=[CH:40][C:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:36]([CH3:35])[CH:37]=1)[C@H:19]([CH2:27][CH2:28][CH3:29])[C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])=[O:17])[C:4]([NH:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:5]
参加物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 6342AcetonitrileHCID 99648454-Bromo-2-methylbiphenylHCID 59875781tert-butyl (2S, 3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-(1-propyl)hex-5-enoate

生成物 1

HCID 59875741tert-butyl (2S,3R,5E)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]-2-(1-propyl)hex-5-enoate収率 63%

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒

実験手順

According to the method of Preparation 3, tert-butyl (2S, 3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-(1-propyl)hex-5-enoate (543 mg, 1.15 mmol) was reacted with 3-methyl-4-phenylbromobenzene (356 mg, 1.44 mmol) under palladium catalysis in a mixture of anhydrous acetonitrile and dimethylformamide (2:5, 7 mL) at 90° C. for 17 h. The mixture was concentrated under reduced pressure, poured into ethyl acetate (100 mL) and washed with water (2×100 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate) to give mainly tert-butyl (2S,3R,5E)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]-2-(1-propyl)hex-5-enoate as a colourless gum (460 mg, 63%). 1H nmr suggested that two alkene isomers, the (5Z) and (4E) were also present. The mixture of alkenes was taken onto the next step (see c, below).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionpoured into ethyl acetate (100 mL)
  3. washwashed with water (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-350010478e034048bcc6286ca651fae1
出典データセット
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06350907B1

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート