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Ethanol → 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 703606
ノート
印刷プレビュー

反応式

HRID 703606 の反応式
C(OC(N1C[C@@H](S[C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H](O)C)[C:14]=2[C:25]([O:27]CC=C)=[O:26])C[C@H]1COCCF)=O)C=C.N1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)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.O1CCCC1>[CH3:20][CH:19]1[CH:18]2[N:15]([C:16](=[O:24])[CH2:17]2)[C:14]([C:25]([OH:27])=[O:26])=[CH:13]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 702EthanolHCID 8083MorpholineHCID 11776TriphenylphosphineHCID 57017483allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

生成物 1

HCID 178370354-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid収率 87.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Tetrakis(triphenylphosphine)palladium(0) [0.32 g) was added to a solution of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.35 g), morpholine (0.84 ml) and triphenylphosphine (0.24 g) in a mixture of water (3 ml), ethanol (12 ml) and tetrahydrofuran (35 ml) at ambient temperature in a stream of nitrogen, and the mixture was stirred at the same condition for 2 hours to give precipitates. The precipitates were collected by filtration, washed with tetrahydrofuran, and dried over phosphorus pentoxide to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)1-hydroxyethyl[-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.67 g).

後処理

  1. customto give
  2. customprecipitates
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with tetrahydrofuran
  5. dry with materialdried over phosphorus pentoxide

出典と根拠

ORDレコード
ord-00f3ec74c16c40cc9c5026fee3c6d919
出典データセット
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04983596

反応ノート

読み込み中…

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