4-Nitrobenzyl chloroformate → HCID 86753539, compound

HRID 342296Notes

Reaction equation

HRID 342296 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([CH2:8][C:9]([S:11][C@H:12]2[CH2:16][CH2:15][N:14]([C:17](=[N:19][C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])[CH3:18])[CH2:13]2)=[O:10])[N:6]([C:33]([C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=2)=[O:38])=[C:34]([CH3:36])[CH3:35])[C:5]1=[O:50])[CH3:3].[N+:51]([C:54]1[CH:64]=[CH:63][C:57]([CH2:58][O:59][C:60](Cl)=[O:61])=[CH:56][CH:55]=1)([O-:53])=[O:52]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N+:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:23][O:22][C:20]([N:19]=[C:17]([N:14]2[CH2:15][CH2:16][C@H:12]([S:11][C:9]([CH2:8][C@H:7]3[N:6]([C:33]([C:37]([O:39][CH2:40][C:41]4[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][CH:46]=4)=[O:38])=[C:34]([CH3:35])[CH3:36])[C:5](=[O:50])[C@@H:4]3[C@H:2]([O:1][C:60]([O:59][CH2:58][C:57]3[CH:56]=[CH:55][C:54]([N+:51]([O-:53])=[O:52])=[CH:64][CH:63]=3)=[O:61])[CH3:3])=[O:10])[CH2:13]2)[CH3:18])=[O:21])=[CH:29][CH:28]=1)([O-:32])=[O:31]

Participants

5

Reactant 2

HCID 782054-Nitrobenzyl chloroformateHCID 86753540HCID 86753540, compound

Product 1

HCID 86753539HCID 86753539, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

56 mg (0.079 mmole) of (3S, 4R)-3-[(R)-1-hydroxyethyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidin-3-ylthio]carbonylmethyl)-1-[2-methyl-1-(p-nitrobenzyloxycarbonyl)prop-1-enyl]-2-azetidinone were dissolved in 1.5 ml of methylene chloride. To the solution were added, in turn, 29 mg (0.24 mmole) of 4-(N,N-dimethylamino)pyridine and 51 mg (0.24 mmole) of p-nitrobenzyloxycarbonyl chloride, with stirring at 0° C. The reaction mixture was stirred at room temperature for 3 hours, diluted with methylene chloride, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulphate. The solvent was distilled off and the residue was subjected to thin layer chromatography using silica gel, developed with a 1:5 by volume mixture of hexane and ethyl acetate, to afford 30 mg (yield 42%) of the title product as an oily substance. 8 mg (14%) of the starting material was also recovered.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. washwashed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulphate
  4. distillationThe solvent was distilled off
  5. additiondeveloped with a 1:5 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-9820e22f22124d1ea60596fca526a5aa
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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