Tetrahydrofuran → Silver

HRID 615117Notes

Reaction equation

HRID 615117 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([N:15]1[CH:21]2[CH:17]([N:18]=[C:19]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:20]2)[C:16]1=[O:30])[N:12]=[N+:13]=[N-:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[Ag+:36].[O:37]1CCCC1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Ag:36].[N:12]([CH:11]([N:15]1[CH:21]([SH:20])[CH:17]([NH:18][C:19](=[O:37])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]1=[O:30])[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[N+:13]=[N-:14]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 159722Silver tetrafluoroborateHCID 14230812HCID 14230812, compound

Product 2

HCID 23954SilverHCID 14230814HCID 14230814, compound

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

To a cooled solution of 7-(1-benzyloxycarbonyl-1-azidomethyl)-3-phenoxymethyl-6-oxo-2-thia-4,7-diazabicyclo[3,2,0]hept-3-ene (3.0 g.) in tetrahydrofuran (48 ml.) was added silver tetrafluoroborate (2.05 g.), followed by a solution of p-toluenesulfonic acid (145.8 mg.) in water (8.1 mg.). After the resultant mixture was stirred at 0° C. for 9 hours, it was concentrated to a volume of 10 ml. To the concentrate was added a mixture of methanol (5 ml.) and water (10 ml.) and precipitates were triturated, filtered and washed with water (three times), a mixture of methanol (5 ml.) and water (10 ml.) (several times), methanol, diethyl ether and hexane, successively to give silver salt at the mercapto group of benzyl 2-azido-2-(3-phenoxyacetamido-4-mercapto-2-oxo-1-azetidinyl)acetate (3.75 g.).

Workup

  1. concentrationit was concentrated to a volume of 10 ml
  2. additionTo the concentrate was added
  3. additiona mixture of methanol (5 ml.) and water (10 ml.)
  4. customprecipitates
  5. customwere triturated
  6. filtrationfiltered
  7. washwashed with water (three times)
  8. additiona mixture of methanol (5 ml.) and water (10 ml.) (several times), methanol, diethyl ether and hexane

Sources & evidence

ORD record
ord-9b6b7a700cda4cc79ebe052ab5be6f14
Source dataset
uspto-grants-1985_02
Patent number
US04497738

Reaction notes

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