Ethyl Acetate → methyl N-[(4'-nitro-1,1'-biphenyl-4-yl)sulfonyl]-L-valinate

HRID 29281

反応式

HRID 29281 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N+:20]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([O-:22])=[O:21].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>COCCOC.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.O>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 27735524-Nitrophenylboronic acidHCID 47337186methyl N-[(4-bromophenyl)sulfonyl]-L-valinate

生成物 1

HCID 10069077methyl N-[(4'-nitro-1,1'-biphenyl-4-yl)sulfonyl]-L-valinate収率 81%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 0.175 g (0.5 mmol) of methyl N-[(4-bromophenyl)sulfonyl]-L-valinate, 0.25 g (1.5 mmol) of 4-nitrophenylboronic acid, 0.087 g of tetrakis(triphenylphosphine)palladium and 8 mL of saturated sodium bicarbonate in 8 mL of ethylene glycol dimethyl ether were refluxed for 2 h, then cooled to room temperature. To the reaction was added 50 mL of ethyl acetate and 40 mL of water. The water layer was extracted with ethyl acetate. The combined ethyl acetate layers was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography, eluting with hexane:ethyl acetate (2:1) to provide 0.159 g of methyl N-[(4′-nitro-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate as a yellow solid. Yield 81%. m.p. 144-146° C.; MS: 391.0(M−H)−.

後処理

  1. temperaturewere refluxed for 2 h
  2. extractionThe water layer was extracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate layers was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexane:ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-0a555bc7f2294e2684f21f1665cd84dc
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

関連ノート

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