Sodium Bicarbonate → HCID 13422897, compound

HRID 2290427Notes

Reaction equation

HRID 2290427 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 13422897HCID 13422897, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-415b235123c34098acf13e3fd06f5162
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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