Diphenylphosphinic chloride → HCID 10700344, compound

HRID 1033671Notes

Reaction equation

HRID 1033671 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[CH:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])[C:8](=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(O)(=O)=O.FC(F)(F)S(O)(=O)=O.[SH:67][C@@H:68]1[CH2:72][N:71]([C:73]([O:75][CH2:76][C:77]2[CH:82]=[CH:81][C:80]([N+:83]([O-:85])=[O:84])=[CH:79][CH:78]=2)=[O:74])[C@H:70]([C:86]([N:88]2[CH2:94][CH2:93][CH2:92][N:91]([CH3:95])[CH2:90][CH2:89]2)=[O:87])[CH2:69]1>C(#N)C>[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)=[O:13])=[C:8]([S:67][C@@H:68]3[CH2:72][N:71]([C:73]([O:75][CH2:76][C:77]4[CH:82]=[CH:81][C:80]([N+:83]([O-:85])=[O:84])=[CH:79][CH:78]=4)=[O:74])[C@H:70]([C:86]([N:88]4[CH2:94][CH2:93][CH2:92][N:91]([CH3:95])[CH2:90][CH2:89]4)=[O:87])[CH2:69]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 4

HCID 73910Diphenylphosphinic chlorideHCID 81531Diisopropylethylamine2×HCID 98853021-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-, (4-nitrophenyl)methyl ester, (4R,5R,6S)-HCID 22851540HCID 22851540, compound

Product 1

HCID 10700344HCID 10700344, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

340 mg of 4-nitrobenzyl (1R, 5R, 6S)-6[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate were dissolved in 3.5 ml of anhydrous acetonitrile, and the solution was placed on an ice bath. Whilst the solution was still on the ice bath, 210 μl of diphenylphosphoryl chloride and 180 μl of diisopropylethylamine were added dropwise to it, and the resulting mixture was stirred for 1 hour at this ice-cooled temperature. 580 μl of diisopropylethylamine and 5 ml of an anhydrous acetonitrile solution containing 640 mg of (2S, 4S)-4-mercapto-2-(4-methyl-1-homopiperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate) [prepared as described in step (1) above] were then added dropwise to the reaction mixture, still on an ice bath, and the resulting mixture was stirred overnight at this ice-cooled temperature. At the end of this time, the mixture was treated and purified by means similar to those described in Example 1(2), to give 316 mg of the title compound.

Workup

  1. customthe solution was placed on an ice bath
  2. additionwere added dropwise to it
  3. temperaturecooled temperature
  4. additionwere then added dropwise to the reaction mixture, still on an ice bath
  5. temperaturecooled temperature
  6. additionAt the end of this time, the mixture was treated
  7. custompurified by means similar to

Sources & evidence

ORD record
ord-3e7747c698254a85bbdcd9c3af715d33
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

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