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Triphenylphosphine → (5R,6S)-3-[1-allylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 1029693
ノート
印刷プレビュー

反応式

HRID 1029693 の反応式
C(O[C:5]([N:7]1[CH2:11][CH2:10][CH:9]([C:12]2[CH2:18][C@H:17]3[N:14]([C:15](=[O:22])[C@@H:16]3[C@H:19]([OH:21])[CH3:20])[C:13]=2[C:23]([O:25]CC=C)=[O:24])[CH2:8]1)=O)C=C.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:30]=1.C(OCC)(=O)CCCCC.[Na]>O1CCCC1.C(O)C.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>[CH2:5]([N:7]1[CH2:11][CH2:10][CH:9]([C:12]2[CH2:18][C@H:17]3[N:14]([C:15](=[O:22])[C@@H:16]3[C@H:19]([OH:21])[CH3:20])[C:13]=2[C:23]([OH:25])=[O:24])[CH2:8]1)[CH:29]=[CH2:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 15117368allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateHCID 53628222Sodium 2-ethyl hexanoate

生成物 1

HCID 15117483(5R,6S)-3-[1-allylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid収率 267.5%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 702Ethanol溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.24 g) in a mixture of tetrahydrofuran (20 ml) and ethanol (5 ml) were added triphenylphosphine (0.16 g), sodium 2-ethyl hexanoate (1.1 g), and tetrakis(triphenylphosphine)palladium(0) (0.37 g). After stirring at ambient temperature for 1 hour, the reaction mixture was washed with dichloromethane, and evaporated in vacuo. The residue was chromatographed on nonionic adsorption resin "Dialon HP-20" eluting with a mixture of water and acetonitrile (95:5, V/V). The fractions containing the desired compound were collected and lyophilized to give (5R,6S)-3-[1-allylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (500 mg).

後処理

  1. washthe reaction mixture was washed with dichloromethane
  2. customevaporated in vacuo
  3. customThe residue was chromatographed on nonionic adsorption resin "Dialon
  4. wash" eluting with a mixture of water and acetonitrile (95:5, V/V)
  5. additionThe fractions containing the desired compound
  6. customwere collected

出典と根拠

ORDレコード
ord-a092a3902e304d97b9fe9a97c53d22b5
出典データセット
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05102877

反応ノート

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