Boron trifluoride etherate → HCID 13422895、化合物

HRID 2290425ノート

反応式

HRID 2290425 の反応式
B(F)(F)F.CCOCC.[C:10]1([C:16]2[O:22][C@H:21]3[C@H:18]([C:19](=[O:23])[NH:20]3)[N:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH:24][CH2:25][C:26]#[C:27][C:28]([O:30][CH3:31])=[O:29].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]([NH:17][C@@H:18]1[C@@H:21]([O:24][CH2:25][C:26]#[C:27][C:28]([O:30][CH3:31])=[O:29])[NH:20][C:19]1=[O:23])(=[O:22])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 8000Boron trifluoride etherateHCID 325086Methyl 4-hydroxybut-2-ynoateHCID 516892Sodium BicarbonateHCID 13276951HCID 13276951、化合物

生成物 1

HCID 13422895HCID 13422895、化合物収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.41 ml of boron trifluoride etherate was added to a suspension of 4.70 g (25 mmols) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one and 14.3 g (125 mmols--5 equivalents) of methyl 4-hydroxy-2-butinoate (R. A. Earl, Organic Synthese 60, 81) in 40 ml of anhydrous methylene chloride at room temperature. The mixture was stirred at room temperature for 1 hour, whereupon a clear solution formed. The solution was then poured into dilute NaHCO3 solution, the mixture was extracted with methylene chloride and the extracts were washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been filtered on 120 g of silica gel (toluene:ethyl acetate 2:3), 4.74 g (63%) of methyl 4-[3(R)-benzoylamino-2-azetidinon-4(R)-yloxy]-2-butinoate were obtained as colorless crystals, melting point: 142°-143° C, RF : 0.29 (toluene:ethyl acetate 2:3), [α]D20 =18.37° (1.0345 percent in acetone).

後処理

  1. customat room temperature
  2. customformed
  3. extractionthe mixture was extracted with methylene chloride
  4. washthe extracts were washed with water
  5. dry with materialdried over MgSO4
  6. customAfter the solvent had been evaporated off in vacuo
  7. filtrationthe residue had been filtered on 120 g of silica gel (toluene:ethyl acetate 2:3)

出典と根拠

ORDレコード
ord-48f199996c6d4bc28d8a243631a83ff8
出典データセット
uspto-grants-1986_10
特許番号
US04616084

反応ノート

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