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

3-Tolylboronic acid → Boc-4-(3-methylphenyl)-L-phenylalanine

HRID 333339
ノート
印刷プレビュー

反応式

HRID 333339 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>COCCOC.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]([O:16][C:14]([NH:13][C@@H:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:21])[CH:27]=2)=[CH:3][CH:4]=1)[C:10]([OH:12])=[O:11])=[O:15])([CH3:20])([CH3:19])[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 27339503-Tolylboronic acidHCID 2734477(2S)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

生成物 1

HCID 68751848Boc-4-(3-methylphenyl)-L-phenylalanine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

(S)-3-(4-bromophenyl)-2-(tert-butoxycarbonylamino)propanoic acid (2.0 g, 5.81 mmol), 3-methylphenylboronic acid (0.948 g, 6.97 mmol), Pd(PPh3)4 (0.336 g, 0.291 mmol) and 2M NaCO3 aqueous solution (4.36 mL) were stirred in 1,2-dimethoxyethane (30 mL) at 80° C. for 2.5 hours. After being cooled to room temperature, the reaction mixture was diluted with EtOAc and washed with 1M HCl and brine. The organic layer was dried over Na2SO4, concentrated under reduced pressure, and purified by silica gel flash column chromatography (10% MeOH in DCM/DCM) to give(S)-2-(tert-butoxycarbonylamino)-3-(3′-methylbiphenyl-4-yl)propanoic acid. MS: m/z (MH+-Boc) 256. Retention time=1.45 min. (condition A).

後処理

  1. washwashed with 1M HCl and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel flash column chromatography (10% MeOH in DCM/DCM) to give(S)-2-(tert-butoxycarbonylamino)-3-(3′-methylbiphenyl-4-yl)propanoic acid

出典と根拠

ORDレコード
ord-3d8091614433457d991cdf74abad3e9f
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877815B2

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