Diphenyl chlorophosphate → HCID 57253095, compound

HRID 1033685Notes

Reaction equation

HRID 1033685 reaction equation
P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C(N(C(C)C)CC)(C)C.[OH:27][C@@H:28]([C@H:30]1[C:51](=[O:52])[N:32]2[CH:33]([C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=3)=[O:39])[C:34](=O)[C@H:35]([CH3:36])[C@H:31]12)[CH3:29].FC(F)(F)S(O)(=O)=O.[C:61]([O:64][CH2:65][CH2:66][N:67]1[CH2:73][CH2:72][CH2:71][N:70]([C:74]([C@@H:76]2[CH2:80][C@H:79]([SH:81])[CH2:78][N:77]2[C:82]([O:84][CH2:85][C:86]2[CH:91]=[CH:90][C:89]([N+:92]([O-:94])=[O:93])=[CH:88][CH:87]=2)=[O:83])=[O:75])[CH2:69][CH2:68]1)(=[O:63])[NH2:62]>C(#N)C>[C:61]([O:64][CH2:65][CH2:66][N:67]1[CH2:73][CH2:72][CH2:71][N:70]([C:74]([C@@H:76]2[CH2:80][C@H:79]([S:81][C:34]3[C@H:35]([CH3:36])[C@@H:31]4[C@@H:30]([C@H:28]([OH:27])[CH3:29])[C:51](=[O:52])[N:32]4[C:33]=3[C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=3)=[O:39])[CH2:78][N:77]2[C:82]([O:84][CH2:85][C:86]2[CH:87]=[CH:88][C:89]([N+:92]([O-:94])=[O:93])=[CH:90][CH:91]=2)=[O:83])=[O:75])[CH2:69][CH2:68]1)(=[O:63])[NH2:62]

Participants

6

Reactant 4

HCID 75654Diphenyl chlorophosphateHCID 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 22851534HCID 22851534, compound

Product 1

HCID 57253095HCID 57253095, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

88 μl of diphenyl chlorophosphate and 74 μl of diisopropylethylamine were added dropwise, whilst ice-cooling, to a solution of 145 mg of 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-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. 202 μl of diisopropylethylamine and a solution of 310 mg of (2S,4S)-2-[4-(2-carbamoyloxyethyl)-1-homopiperazinylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethanesulfonate [prepared as described in step (1) above] in 2.0 ml of anhydrous acetonitrile were then added dropwise to the mixture, whilst ice-cooling, and the resulting mixture was allowed to stand overnight at the same temperature. At the end of this time, the reaction mixture was worked up and purified in a similar manner to that described in Example 32(2), to afford 107 mg of the title compound as a powder.

Workup

  1. temperaturecooling
  2. waitto stand overnight at the same temperature
  3. custompurified in a similar manner to that

Sources & evidence

ORD record
ord-e58effd8dcda4ec7a32013d89b9353c1
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

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