Sodium Bicarbonate → HCID 13422897、化合物

HRID 2290427ノート

反応式

HRID 2290427 の反応式
[B].[C:2]1([C:8]2[O:14][C@H:13]3[C@H:10]([C:11](=[O:15])[NH:12]3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:16][CH2:17][C:18]#[C:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:21].C([O-])(O)=O.[Na+]>O1CCCC1>[C:8]([NH:9][C@@H:10]1[C@@H:13]([O:16][CH2:17][C:18]#[C:19][C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)=[O:21])[NH:12][C:11]1=[O:15])(=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 5462311BoronHCID 13276951HCID 13276951、化合物HCID 13422898(4-Nitrophenyl)methyl 4-hydroxybut-2-ynoate

生成物 1

HCID 13422897HCID 13422897、化合物収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

10 μl of boron trifuloride etherate were sprayed into a stirred suspension of 376 mg (2mmols) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one and 941 mg (4 mmols) of 4-nitrobenzyl 4-hydroxy-2-butinoate in 8 ml of anhydrous tetrahydrofuran at room temperature. After a short time, a clear, light yellow solution formed, and was stirred at room temperature for 0.5 hour. Thereafter, the solution was poured into dilute NaHCO3 solution, the mixture was extracted with methylene chloride and the extract was washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been chromatographed on 60 g of silica gel (toluene:ethyl acetate 35:65), 557 mg (66%) of 4-nitrobenzyl 4-[3(R)-benzoylamino-2-azetidinon-4(R)-yloxy]-2-butinoate were obtained as a colorless rigid foam.

後処理

  1. customAfter a short time, a clear, light yellow solution formed
  2. extractionthe mixture was extracted with methylene chloride
  3. washthe extract was washed with water
  4. dry with materialdried over MgSO4
  5. customAfter the solvent had been evaporated off in vacuo
  6. customthe residue had been chromatographed on 60 g of silica gel (toluene:ethyl acetate 35:65)

出典と根拠

ORDレコード
ord-415b235123c34098acf13e3fd06f5162
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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