Sodium Bicarbonate → HCID 13422897, 화합물

HRID 2290427노트

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HRID 2290427 반응식
[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

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5462311BoronHCID 13276951HCID 13276951, 화합물HCID 13422898(4-Nitrophenyl)methyl 4-hydroxybut-2-ynoate

생성물 1

HCID 13422897HCID 13422897, 화합물수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-415b235123c34098acf13e3fd06f5162
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04616084

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