4-Nitrobenzyl chloroformate → HCID 86753537, compound

HRID 342293Notes

Reaction equation

HRID 342293 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([CH2:8][C:9]([S:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])=[O:10])[N:6]([C:28]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=2)=[O:33])=[C:29]([CH3:31])[CH3:30])[C:5]1=[O:45])[CH3:3].[N+:46]([C:49]1[CH:59]=[CH:58][C:52]([CH2:53][O:54][C:55](Cl)=[O:56])=[CH:51][CH:50]=1)([O-:48])=[O:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:15]([NH:14][CH2:13][CH2:12][S:11][C:9]([CH2:8][C@H:7]2[N:6]([C:28]([C:32]([O:34][CH2:35][C:36]3[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=3)=[O:33])=[C:29]([CH3:30])[CH3:31])[C:5](=[O:45])[C@@H:4]2[C@H:2]([O:1][C:55]([O:54][CH2:53][C:52]2[CH:51]=[CH:50][C:49]([N+:46]([O-:48])=[O:47])=[CH:59][CH:58]=2)=[O:56])[CH3:3])=[O:10])=[O:16])=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

5

Reactant 2

HCID 782054-Nitrobenzyl chloroformateHCID 86753538HCID 86753538, compound

Product 1

HCID 86753537HCID 86753537, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

125 mg (0.194 mmole) of (3S, 4R)-3-[(R)-1-hydroxyethyl]-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]-carbonylmethyl)-1-[2-methyl-1-(p-nitrobenzyloxycarbonyl)-prop-1-enyl]-2-azetidinone were dissolved in 4 ml of methylene chloride. To the solution were added, in turn, 71 mg (0.58 mmole) of 4-(N,N-dimethylamino)-pyridine and 126 mg (0.58 mmole) of p-nitrobenzyloxy-carbonyl chloride, with stirring at 0° C. The reaction mixture was then stirred at room temperature for 1 hour, after which it was diluted with methylene chloride and washed with a saturated aqueous solution of sodium chloride. The solvent was distilled off and the residue was subjected to chromatography using a Lobar column B eluted with a 2:3 by volume mixture of hexane and ethyl acetate, to afford 82 mg (yield 51%) of the title product as an oily substance. Infra-red and nuclear magnetic resonance spectra of the product agreed with those of the product of Preparation 7.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 1 hour
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. distillationThe solvent was distilled off
  4. washeluted with a 2:3 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b9f53b50101b4841aaca6a14fb70fd84
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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