Triisopropyl phosphite → HCID 86742126, compound

HRID 649553Notes

Reaction equation

HRID 649553 reaction equation
[C:1]([C@@H:4]1[CH2:8][C@H:7]([S:9][C:10]([CH2:12][C@H:13]2[N:16]([C:17](=O)[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])[C:15](=[O:32])[C@@H:14]2[C@H:33]([O:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])[CH3:34])=[O:11])[CH2:6][N:5]1[C:49](=[N:51][C:52]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=1)=[O:53])[CH3:50])(=[O:3])[NH2:2].[P:65]([O:74][CH:75]([CH3:77])[CH3:76])([O:70][CH:71]([CH3:73])[CH3:72])[O:66][CH:67]([CH3:69])[CH3:68]>C1(C)C=CC=CC=1>[C:1]([C@@H:4]1[CH2:8][C@H:7]([S:9][C:10]([CH2:12][C@H:13]2[N:16]([C:17]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[P:65]([O:70][CH:71]([CH3:73])[CH3:72])([O:74][CH:75]([CH3:77])[CH3:76])[O:66][CH:67]([CH3:69])[CH3:68])[C:15](=[O:32])[C@@H:14]2[C@H:33]([O:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])[CH3:34])=[O:11])[CH2:6][N:5]1[C:49](=[N:51][C:52]([O:54][CH2:55][C:56]1[CH:57]=[CH:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=1)=[O:53])[CH3:50])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 8304Triisopropyl phosphiteHCID 86742127HCID 86742127, compound

Product 1

HCID 86742126HCID 86742126, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

454 mg (0.5 mmole) of (3S,4R)-4-{[(2S,4S)-2-carbamoyl-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidin-4-ylthio]carbonylmethyl}-3-[1(R)-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-(p-nitrobenzyloxyoxalyl)-2-azetidinone and 520 mg (2.5 mmole) of triisopropyl phosphite were dissolved in 10 ml of toluene. The solution was heated in a stream of a nitrogen gas at 90° C. for 2 hours. The solvent was then distilled off under reduced pressure. The residue was subjected to chromatography using a Lobar column eluted with a 30:10:1 by volume mixture of ethyl acetate, chloroform and methanol, to afford 330 mg (yield 60%) of the title product as an oily substance.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. washeluted with a 30:10:1 by volume mixture of ethyl acetate, chloroform and methanol

Sources & evidence

ORD record
ord-26dc9381472649838cde128e33129197
Source dataset
uspto-grants-1988_04
Patent number
US04740507

Reaction notes

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