4-Nitrobenzyl chloroformate → HCID 86753536, compound

HRID 342292Notes

Reaction equation

HRID 342292 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([CH2:8][C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[N:6]([C:18]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:23])=[C:19]([CH3:21])[CH3:20])[C:5]1=[O:35])[CH3:3].[N+:36]([C:39]1[CH:49]=[CH:48][C:42]([CH2:43][O:44][C:45](Cl)=[O:46])=[CH:41][CH:40]=1)([O-:38])=[O:37].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:20][C:19]([CH3:21])=[C:18]([N:6]1[C@H:7]([CH2:8][C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[C@@H:4]([C@H:2]([O:1][C:45]([O:44][CH2:43][C:42]2[CH:41]=[CH:40][C:39]([N+:36]([O-:38])=[O:37])=[CH:49][CH:48]=2)=[O:46])[CH3:3])[C:5]1=[O:35])[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=1)=[O:23]

Participants

6

Reactant 3

HCID 782054-Nitrobenzyl chloroformateHCID 516892Sodium BicarbonateHCID 86753534HCID 86753534, compound

Product 1

HCID 86753536HCID 86753536, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

44 mg (0.088 mmole) of (3S, 4R)-3-[(R)-1-hydroxyethyl]-1-[2-methyl-1-(p-nitrobenzyloxycarbonyl)prop-1-enyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone were dissolved in 2 ml of methylene chloride. To the solution were added 32 mg (0.26 mmole) of 4-(N,N-dimethylamino)pyridine and 57 mg (0.26 mmole) of p-nitrobenzyloxycarbonyl chloride, with stirring at 0° C. The mixture was stirred at that temperature for 3 hours, after which it was poured into a dilute aqueous solution of sodium bicarbonate and extracted with chloroform. The chloroform extract was washed successively with dilute hydrochloric acid and a dilute aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulphate. The solvent was then distilled off. The residue was subjected to thin layer chromatography using silica gel developed with a 3:1 by volume mixture of benzene and ethyl acetate, to afford 21 mg (yield 35%) of the title product as an oil.

Workup

  1. stirringThe mixture was stirred at that temperature for 3 hours
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. washwas washed successively with dilute hydrochloric acid
  5. dry with materiala dilute aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulphate
  6. distillationThe solvent was then distilled off
  7. additiondeveloped with a 3:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-eb75a7a4bf874876b5adb6ea7a415a7d
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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