Hydrochloric Acid → 1-Benzyl-4-ethynyl-3-(1-hydroxyethyl)-2-azetidinone

HRID 247702

反応式

HRID 247702 の反応式
C1(S[O:8][C:9](=O)[CH:10]([CH:26]([OH:28])[CH3:27])[CH:11]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]#[C:13][Si](C)(C)C)C=CC=CC=1.[OH-].[K+].Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=C(SSC2N=CC=CC=2)N=CC=1>C1COCC1.C(#N)C>[CH2:19]([N:18]1[CH:11]([C:12]#[CH:13])[CH:10]([CH:26]([OH:28])[CH3:27])[C:9]1=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 650932,2'-Dipyridyl disulfideHCID 545323513-Benzylamino-2-(1-hydroxyethyl)-5-trimethylsilyl-4-pentinic acid phenylthio ester

生成物 1

HCID 139595611-Benzyl-4-ethynyl-3-(1-hydroxyethyl)-2-azetidinone

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

There was dissolved 2.054 g (5.0 mmol) of 3-benzylamino-2-(1-hydroxyethyl)-5-trimethylsilyl-4-pentinic acid phenylthioester in 40 ml of THF, to which 3 ml of 4 N potassium hydroxide was added and the mixture was stirred at room temperature for 3 hours. The reaction mixture was neutralized with 2 N hydrochloric acid and was extracted six times with ethyl acetate while conducting salting-out. The extract was dried with anhydrous magnesium sulfate and concentrated. There was added 250 ml of acetonitrile to the concentrated solution, and then 1.57 g (60 mmol) of triphenylphosphine was added, to which 1.32 g (6.0 mmol) of 2,2'-dipyridyldisulfide in 50 ml of acetonitrile was added dropwise for 40 minutes while vigorously stirring with heating under reflux. After the solution was further heated under reflux for 1 hour, the obtained reaction mixture was concentrated, followed by purification with 50 g of silica-gel column-chromatography (eluent; methylene chloride→diethyl ether) and then with 50 g of silica-gel column-chromatography (eluent;hexane:diethyl ether=1:4) to give 801 mg of a trans-form and 62 mg of a cis-form of 1-benzyl-4-ethynyl-3-(1-hydroxyethyl)-2-azetidinone.

後処理

  1. extractionwas extracted six times with ethyl acetate
  2. dry with materialThe extract was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. additionThere was added 250 ml of acetonitrile to the concentrated solution
  5. additionwas added dropwise for 40 minutes
  6. stirringwhile vigorously stirring
  7. temperaturewith heating
  8. temperatureunder reflux
  9. temperatureAfter the solution was further heated
  10. temperatureunder reflux for 1 hour
  11. customthe obtained reaction mixture
  12. concentrationwas concentrated
  13. customfollowed by purification with 50 g of silica-gel column-chromatography (eluent; methylene chloride→diethyl ether)

出典と根拠

ORDレコード
ord-74f19f2684e14a59a7a5c52e15c17844
出典データセット
uspto-grants-1987_11
特許番号
US04709064

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