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

HRID 1029689
ノート
印刷プレビュー

反応式

HRID 1029689 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3].Cl.[CH:21](=[NH:30])OCC1C=CC=CC=1.[OH-].[Na+].Cl>>[CH:21]([N:17]1[CH2:18][CH2:19][CH:15]([C:7]2[CH2:6][C@H:5]3[N:9]([C:10](=[O:11])[C@@H:4]3[C@H:2]([OH:1])[CH3:3])[C:8]=2[C:12]([OH:14])=[O:13])[CH2:16]1)=[NH:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13116802Benzyl formimidate hydrochlorideHCID 15117376(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(pyrrolidin-3-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

生成物 1

HCID 15117383(5R,6S)-3-(1-formimidoylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid収率 43.6%

実験手順

To a solution of (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(pyrrolidin-3-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (250 mg) was added benzyl formimidate hydrochloride (0.48 g) at 0° C. while adjusting pH to 8.5 with 30% aqueous sodium hydroxide solution. After 30 minutes at the same temperature, the solution was adjusted to pH 6.5 with 1N hydrochloric acid, washed with ethyl acetate and concentrated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" (Trademark, made by Mitsubishi Chemical Industries) eluting with 3% aqueous isopropyl alcohol. The fractions containing the desired compound were collected and lyophilized to give (5R,6S)-3-(1-formimidoylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (120 mg).

後処理

  1. washwashed with ethyl acetate
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on nonionic adsorption resin "Diaion
  4. wash" (Trademark, made by Mitsubishi Chemical Industries) eluting with 3% aqueous isopropyl alcohol
  5. additionThe fractions containing the desired compound
  6. customwere collected

出典と根拠

ORDレコード
ord-2c2bccfc18444db28ad06482d2c19460
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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