4-Nitrobenzyl chloroformate → HCID 10907392, compound

HRID 362111Notes

Reaction equation

HRID 362111 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]([C@@H:8]2[CH2:12][C@H:11]([S:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:10][N:9]2[CH3:23])=[O:7])[CH2:3]1.C(N(C(C)C)CC)(C)C.Cl[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)=[O:35]>C(Cl)Cl.C(OCC)(=O)C>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][S:13][C@@H:11]2[CH2:10][N:9]([CH3:23])[C@H:8]([C:6]([N:4]3[CH2:5][CH:2]([NH:1][C:34]([O:36][CH2:37][C:38]4[CH:39]=[CH:40][C:41]([N+:44]([O-:46])=[O:45])=[CH:42][CH:43]=4)=[O:35])[CH2:3]3)=[O:7])[CH2:12]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 782054-Nitrobenzyl chloroformateHCID 81531DiisopropylethylamineHCID 10991288HCID 10991288, compound

Product 1

HCID 10907392HCID 10907392, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.60 g of (2S, 4S)-2-(3-aminoazetidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (a) above] was dissolved in 18 ml of methylene chloride, and 0.38 ml of diisopropylethylamine and 0.46 g of p-nitrobenzyl chloroformate were added to the resulting solution, whilst ice-cooling, after which the mixture was stirred at the same temperature for 30 minutes. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed with water and with an aqueous solution of sodium chloride, in that order. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to silica gel column chromatography (silica gel 60 9385, manufactured by Merck, 40 g), to give 0.85 g of the title compound, in the form of an amorphous powder, from the fraction obtained by elution with a 95:5 by volume mixture of ethyl acetate and methanol.

Workup

  1. temperaturecooling
  2. washwashed with water and with an aqueous solution of sodium chloride, in that order
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-393b0417dc824b3ab6f6a64c9152fe6b
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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