Diphenylphosphinic chloride → HCID 131720430, compound

HRID 727617Notes

Reaction equation

HRID 727617 reaction equation
C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)CC)(C)C.[OH:25][C@@H:26]([C@H:28]1[C:49](=[O:50])[N:30]2[CH:31]([C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=3)=[O:37])[C:32](=O)[C@H:33]([CH3:34])[C@H:29]12)[CH3:27].FC(F)(F)S(O)(=O)=O.[SH:59][C@@H:60]1[CH2:64][N:63]([CH3:65])[C@H:62]([C:66]([N:68]2[CH2:73][CH2:72][N:71]([C:74]([O:76][CH2:77][C:78]3[CH:83]=[CH:82][C:81]([N+:84]([O-:86])=[O:85])=[CH:80][CH:79]=3)=[O:75])[CH2:70][CH2:69]2)=[O:67])[CH2:61]1>C(#N)C>[N+:84]([C:81]1[CH:82]=[CH:83][C:78]([CH2:77][O:76][C:74]([N:71]2[CH2:72][CH2:73][N:68]([C:66]([C@@H:62]3[CH2:61][C@H:60]([S:59][C:32]4[C@H:33]([CH3:34])[C@@H:29]5[C@@H:28]([C@H:26]([OH:25])[CH3:27])[C:49](=[O:50])[N:30]5[C:31]=4[C:36]([O:38][CH2:39][C:40]4[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=4)=[O:37])[CH2:64][N:63]3[CH3:65])=[O:67])[CH2:69][CH2:70]2)=[O:75])=[CH:79][CH:80]=1)([O-:86])=[O:85]

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 88299975HCID 88299975, compound

Product 1

HCID 131720430HCID 131720430, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

7.0 g of diphenylphosphoryl chloride and 3.4 g of diisopropylethylamine were added dropwise, whilst ice-cooling, to a solution of 8.6 g of 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate in 120 ml of dry acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. 6.7 g of diisopropylethylamine and a solution of 13.8 g of (2S,4S)-4-mercapto-2-[4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-1-methylpyrrolidine trifluoromethanesulfonate in dry acetonitrile were then simultaneously added dropwise to the mixture, whilst ice-cooling, and the resulting mixture was allowed to stand overnight, whilst ice-cooling. At the end of this time, the reaction mixture was worked up and purified in a similar manner to that described in Example 49(a), to give 7.0 g of the title compound, as a powder.

Workup

  1. temperaturecooling
  2. waitto stand overnight, whilst ice-
  3. temperaturecooling
  4. custompurified in a similar manner to that

Sources & evidence

ORD record
ord-645d79e9d1454b16945f839ad6656b72
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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