Diphenylphosphinic chloride → HCID 57320783, compound

HRID 362017Notes

Reaction equation

HRID 362017 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].F[C:52](F)(F)[S:53](O)(=O)=O.FC(F)(F)S(O)(=O)=O.S[C@@H]1[CH2:72][N:71](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:70]([C:86]([N:88]2[CH2:93][CH2:92][N:91]([CH2:94][C:95]([O:97][CH2:98][C:99]3[CH:104]=[CH:103][C:102]([N+:105]([O-:107])=[O:106])=[CH:101][CH:100]=3)=[O:96])[CH2:90][CH2:89]2)=[O:87])[CH2:69]1>C(#N)C>[N+:105]([C:102]1[CH:101]=[CH:100][C:99]([CH2:98][O:97][C:95]([CH2:94][N:91]2[CH2:90][CH2:89][N:88]([C:86]([C@@H:70]3[CH2:69][C@H:52]([S:53][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])[CH2:72][NH:71]3)=[O:87])[CH2:93][CH2:92]2)=[O:96])=[CH:104][CH:103]=1)([O-:107])=[O:106]

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 86753698HCID 86753698, compound

Product 1

HCID 57320783HCID 57320783, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

290 μl of diphenylphosphoryl chloride and 245 μl of diisopropylethylamine were added dropwise, whilst ice-cooling, to a solution of 500 mg of 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate in 5 ml of dry acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. 520 μl of diisopropylethyl-amine and a solution of 1.57 g of (2S,4S)-4-mercapto-2-[4-(4-nitrobenzyloxycarbonylmethyl)-1-piperazinyl-carbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate) (prepared as described in Preparation 56) in 5ml of dry acetonitrile were then simultaneously 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 solvent was removed by distillation under reduced pressure, and the resulting residue was subjected to column chromatography through a Lobar column (Merck, LiChroprep Si60, size B), using with a 5:1 by volume mixture of ethyl acetate and methanol as the eluent. Those fractions containing the title compound were combined and concentrated by evaporation under reduced pressure, to give 706 mg of the title compound, as a powder.

Workup

  1. temperaturecooling
  2. waitto stand overnight at the same temperature
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. additionusing with a 5:1 by volume mixture of ethyl acetate and methanol as the eluent
  5. additionThose fractions containing the title compound
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-95cb211a0321456ab152a0e0b2a93ea6
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

Loading…