Diphenyl chlorophosphate → HCID 131718403, compound

HRID 1033683Notes

Reaction equation

HRID 1033683 reaction equation
C(N(C(C)C)CC)(C)C.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[OH:27][C@@H:28]([C@H:30]1[C:50](=[O:51])[N:32]2[CH:33]([C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=[O:38])[C:34](=O)[CH2:35][C@H:31]12)[CH3:29].FC(F)(F)S(O)(=O)=O.[SH:60][C@@H:61]1[CH2:65][N:64]([C:66]([O:68][CH2:69][C:70]2[CH:75]=[CH:74][C:73]([N+:76]([O-:78])=[O:77])=[CH:72][CH:71]=2)=[O:67])[C@H:63]([C:79]([N:81]2[CH2:86][CH2:85][N:84]([CH3:87])[CH2:83][CH2:82]2)=[O:80])[CH2:62]1>C(#N)C>[OH:27][C@@H:28]([C@H:30]1[C:50](=[O:51])[N:32]2[C:33]([C:37]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][CH:46]=3)=[O:38])=[C:34]([S:60][C@@H:61]3[CH2:65][N:64]([C:66]([O:68][CH2:69][C:70]4[CH:75]=[CH:74][C:73]([N+:76]([O-:78])=[O:77])=[CH:72][CH:71]=4)=[O:67])[C@H:63]([C:79]([N:81]4[CH2:82][CH2:83][N:84]([CH3:87])[CH2:85][CH2:86]4)=[O:80])[CH2:62]3)[CH2:35][C@H:31]12)[CH3:29]

Participants

6

Reactant 4

HCID 75654Diphenyl chlorophosphateHCID 81531Diisopropylethylamine2×HCID 11198839(4-Nitrophenyl)methyl (5R,6S)-6-((1R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo(3.2.0)heptane-2-carboxylateHCID 86747835HCID 86747835, compound

Product 1

HCID 131718403HCID 131718403, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

85 μl of diisopropylethylamine and 86 μl of diphenyl chlorophosphate were simultaneously added, whilst ice-cooling, to a solution of 161 mg of 4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate in 2 ml of anhydrous acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. At the end of this time, 232 μof diisopropylethylamine and a solution of 310 mg of (2S,4S)-4-mercapto-2-(4-methyl-1-piperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethanesulfonate [prepared as described in Example 1(1)] in 2 ml of anhydrous acetonitrile were added dropwise to the mixture, whilst ice-cooling, and the resulting mixture was stirred at the same temperature for 2 hours, after which it was allowed to stand overnight, whilst ice-cooling. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was worked up and purified in a similar manner to that described in Example 29(1), to afford 209 mg of the title compound as a powder.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at the same temperature for 2 hours
  3. waitto stand overnight, whilst ice-
  4. temperaturecooling
  5. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  6. custompurified in a similar manner to that

Sources & evidence

ORD record
ord-490e8b47f3964e8dbf890491abe0d473
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

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