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

HRID 1363463노트

반응식

HRID 1363463 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-630641e897694613a39edb3139fe4c3b
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884204B2

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