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Potassium Carbonate → (R)-3-[N'-t-Butoxycarbonyl-N-(3'-chlorobiphenyl-4-ylmethyl)-hydrazino]-2-hydroxy-propionic Acid

HRID 2272634
ノート
印刷プレビュー

反応式

HRID 2272634 の反応式
C[O:2][C:3](=[O:24])[C@H:4]([OH:23])[CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1)[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.[Cl-].[NH4+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:11]([O:10][C:8]([NH:7][N:6]([CH2:5][C@@H:4]([OH:23])[C:3]([OH:2])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:25])[CH:31]=2)=[CH:18][CH:17]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]
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

8

反応物 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 67972599(R)-3-[N-(4-Bromobenzyl)-N'-t-butoxycarbonylhydrazino]-2-hydroxypropionic acid methyl ester

生成物 1

HCID 67972781(R)-3-[N'-t-Butoxycarbonyl-N-(3'-chlorobiphenyl-4-ylmethyl)-hydrazino]-2-hydroxy-propionic Acid

試薬・触媒・溶媒 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 25517Ammonium Chloride溶媒

反応条件

温度
90 °C

実験手順

(R)-3-[N-(4-Bromobenzyl)-N′-t-butoxycarbonyl-hydrazino]-2-hydroxy-propionic acid methyl ester (1.0 g, 2.5 mmol), 3-chlorophenylboronic acid (776 mg, 5.0 mmol), and K2CO3 (857 mg, 6.2 mmol) were dissolved in a mixture of THF (18 mL) and water (18 mL). The reaction flask was then purged with nitrogen and tetrakis(triphenylphosphine) palladium(0) (286 mg, 248 μmol) was added. The mixture was stirred at 90° C. overnight (˜18 hours). The mixture was diluted with saturated aqueous ammonium chloride and extracted with EtOAc. The organic layer was collected, dried and concentrated. The product was purified (Interchim reverse phase chromatography column, 10-80% MeCN in water) to yield the title compound.

後処理

  1. additionwas added
  2. extractionextracted with EtOAc
  3. customThe organic layer was collected
  4. customdried
  5. concentrationconcentrated
  6. customThe product was purified (Interchim reverse phase chromatography column, 10-80% MeCN in water)

出典と根拠

ORDレコード
ord-32fc4adffb0a49a186712aa38b41bf85
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09120758B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート