Acetic Acid → HCID 9838554、化合物

HRID 1975485ノート

反応式

HRID 1975485 の反応式
C(O[C:5]([NH:7][CH2:8][CH:9]([C:18]1[CH2:24][C@H:23]2[N:20]([C:21](=[O:28])[C@@H:22]2[C@H:25]([OH:27])[CH3:26])[C:19]=1[C:29]([O:31]CC=C)=[O:30])[CH2:10][NH:11]C(OCC=C)=O)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)CC(=O)CC(=O)C1.C(O)(=O)C>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.C(OCC)(=O)C>[OH:27][C@@H:25]([C@H:22]1[C:21](=[O:28])[N:20]2[C@@H:23]1[CH2:24][C:18]([CH:9]1[CH2:10][N:11]=[CH:5][NH:7][CH2:8]1)=[C:19]2[C:29]([OH:31])=[O:30])[CH3:26]

参加物

9

反応物 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 31358DimedoneHCID 57160014HCID 57160014、化合物

生成物 1

HCID 9838554HCID 9838554、化合物収率 22.8%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
30 °C

実験手順

To a solution of 741 mg of allyl (5R,6S)-3-[2-allyloxycarbonylamino-1-(N-allyloxycarbonylaminomethyl)ethyl]-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate in 9.25 ml of tetrahydrofuran and 3.07 ml of ethanol were added successively 163 mg of triphenylphosphine, 870 mg of dimedone, 0.089 ml of acetic acid and 143 mg of tetrakis(triphenylphosphine)palladium at room temperature under nitrogen. The mixture was stirred at 30° C. for a few minutes, and then stirring was continued at room temperature for 30 minutes. After a pale yellow precipitate was deposited, 2.2 ml of ethyl acetate was added. The precipitate was filtrated and washed with ethyl acetate and dichloromethane under nitrogen, and dissolved in pH 6.86 buffer solution. 399 mg of Benzyl formimidate hydrochloride was added to the solution at 0° C., while the pH was kept at 8.5. After stirring for 1.5 hours at pH 7.0, the reaction mixture was washed five times with 30% tetrahydrofuran in ethyl acetate while the pH was kept at pH 7. Purification was carried out by a column chromatography on "Diaion HP-20" (trademark, made by Mitsubishi Chemical Industries) (eluent: water followed by 2% acetonitrile in water) and silica gel (eluent: 0-30% water in acetonitrile gradiently) successively to give 99 mg of [5R,6S)-6-[(R)-1-hydroxyethyl]-3-[3,4,5,6-tetrahydropyrimidin-5-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

後処理

  1. stirringstirring
  2. filtrationThe precipitate was filtrated
  3. washwashed with ethyl acetate and dichloromethane under nitrogen
  4. dissolutiondissolved in pH 6.86 buffer solution
  5. addition399 mg of Benzyl formimidate hydrochloride was added to the solution at 0° C., while the pH
  6. stirringAfter stirring for 1.5 hours at pH 7.0
  7. washthe reaction mixture was washed five times with 30% tetrahydrofuran in ethyl acetate while the pH
  8. customPurification

出典と根拠

ORDレコード
ord-25714fc4a8844768aa0e01ea6805ee16
出典データセット
uspto-grants-1994_02
特許番号
US05286721

反応ノート

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