4-Nitrobenzyl chloroformate → HCID 57293013, compound

HRID 744879Notes

Reaction equation

HRID 744879 reaction equation
[NH2:1][CH2:2][CH2:3][C@H:4]([OH:8])[C:5]([OH:7])=[O:6].[N+:9]([C:12]1[CH:22]=[CH:21][C:15]([CH2:16][O:17][C:18](Cl)=[O:19])=[CH:14][CH:13]=1)([O-:11])=[O:10]>[OH-].[Na+].CCOCC>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([CH2:16][O:17][C:18]([NH:1][CH2:2][CH2:3][C@H:4]([OH:8])[C:5]([OH:7])=[O:6])=[O:19])=[CH:21][CH:22]=1)([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 782054-Nitrobenzyl chloroformateHCID 27339294-Amino-2-hydroxybutyric acid, (S)-(-)-

Product 1

HCID 57293013HCID 57293013, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A 2.82 g portion of (2S)-4-amino-2-hydroxybutyric acid was dissolved in 15 ml of 2N sodium hydroxide, and to the solution cooled on an ice bath were simultaneously added dropwise 6.13 g of p-nitrobenzyloxycarbonyl chloride dissolved in ether and 7.5 ml of 4N sodium hydroxide. After 2 hours of stirring at the same temperature, the solution was washed with ether, an aqueous layer was adjusted to acidic with concentrated hydrochloric acid, and a precipitated solid material was collected by filtration, washed with water and then dried to yield 4.48 g of (2S)-4-(p-nitrobenzyloxycarbonyl) amino-2-hydroxybutyric acid.

Workup

  1. temperatureto the solution cooled on an ice bath
  2. washthe solution was washed with ether
  3. filtrationa precipitated solid material was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-3129144cf9254342927bb0d2942c50d2
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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