Dicyclohexylcarbodiimide → (3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]-pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

HRID 342286Notes

Reaction equation

HRID 342286 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([OH:18])=O)[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[SH:20][C@H:21]1[CH2:25][CH2:24][N:23]([C:26](=[N:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[CH3:27])[CH2:22]1.C1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:20][C@H:21]2[CH2:25][CH2:24][N:23]([C:26](=[N:28][C:29]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=3)=[O:30])[CH3:27])[CH2:22]2)=[O:18])[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10859145(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-oxoazetidineHCID 54561487(S)-4-Nitrobenzyl (1-(3-mercaptopyrrolidin-1-yl)ethylidene)carbamate

Product 1

HCID 88672952(3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]-pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinoneYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

2.67 mg (0.93 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-azetidinone and 330 mg (1.02 mmole) of (S)-3-mercapto-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidine were dissolved in 5 ml of benzene. 210 mg (9.02 mmole) of dicyclohexylcarbodiimide and 5 mg (0.04 mmole) of 4-dimethylaminopyridine were added, and the mixture was stirred at room temperature for 1 hour, after which insolubles were filtered off. The filtrate was concentrated to dryness by evaporation under reduced pressure and the resulting oily residue was purified by column chromatography through 15 g of silica gel eluted with mixtures of benzene and ethyl acetate in volume ratios from 1:2 to 1:5, to give 495 mg (yield 90%) of the title product in the form of an oil.

Workup

  1. filtrationafter which insolubles were filtered off
  2. concentrationThe filtrate was concentrated to dryness by evaporation under reduced pressure
  3. customthe resulting oily residue was purified by column chromatography through 15 g of silica gel
  4. washeluted with mixtures of benzene and ethyl acetate in volume ratios from 1:2 to 1:5

Sources & evidence

ORD record
ord-9a13408d171e4173ada70bfac45c6727
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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