Triethylamine → methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate

HRID 1363463ノート

反応式

HRID 1363463 の反応式
C(N(CC)CC)C.[CH3:8][C:9]1([CH3:16])[C:13]([CH3:15])([CH3:14])[O:12][BH:11][O:10]1.O1CCOCC1.[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:36][C:37]1[CH:42]=[CH:41][C:40](I)=[CH:39][CH:38]=1)[C:32]([O:34][CH3:35])=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:36][C:37]1[CH:38]=[CH:39][C:40]([B:11]2[O:12][C:13]([CH3:15])([CH3:14])[C:9]([CH3:16])([CH3:8])[O:10]2)=[CH:41][CH:42]=1)[C:32]([O:34][CH3:35])=[O:33])=[O:29])([CH3:26])([CH3:24])[CH3:25]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 10319078N-Boc-4-iodophenylalanine methylester

生成物 1

HCID 10949509methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

PdCl2(dppf) (127 mg), triethylamine (2.14 ml), 4,4,5,5-tetramethyl-1,3,2-dioxaborolan (1.13 ml) and 1,4-dioxane (21 ml) were added to methyl (2S)-2-[(t-butoxycarbonyl)amino]-3-(4-iodophenyl)propionate (1.8 g) and stirred at 100° C. for 14 hours. The reaction solution was diluted with ethyl acetate, washed with water and dried over magnesium sulfate to remove the solvent. The residue was purified with a silica gel chromatography (hexane-ethyl acetate) to obtain the title compound (1.05 g).

後処理

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customto remove the solvent
  4. customThe residue was purified with a silica gel chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-630641e897694613a39edb3139fe4c3b
出典データセット
uspto-grants-2011_02
特許番号
US07884204B2

反応ノート

読み込み中…