4-Nitrobenzyl bromide → HCID 178445560, compound

HRID 1857546Notes

Reaction equation

HRID 1857546 reaction equation
[CH2:1](OC(=O)C(C(OC)P(CC1C=CC([N+]([O-])=O)=CC=1)=O)CC(C)C)C1C=CC=CC=1.[N+:31]([C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1)([O-])=O.[CH2:42]([O:49][C:50]([CH:52]([CH2:57][CH:58]([CH3:60])[CH3:59])[CH2:53][PH:54](=[O:56])[OH:55])=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(O)C.O.Cl.[Fe]>[CH2:42]([O:49][C:50](=[O:51])[CH:52]([CH2:53][PH:54]([O:55][CH2:1][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([NH2:31])=[CH:35][CH:36]=1)=[O:56])[CH2:57][CH:58]([CH3:60])[CH3:59])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

8

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 178445562HCID 178445562, compoundHCID 178494947HCID 178494947, compound

Product 1

HCID 178445560HCID 178445560, compoundYield 53%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-[Methoxy(4-nitrobenzyl) phosphinoylmethyl]-4-methylpentanoic acid benzyl ester (prepared from 4-nitrobenzyl bromide and (2-benzyloxycarbonyl4-methylpentyl)phosphinic acid by the procedure described in Example 1/Step B) (900 mg, 2.08 mmole) in a mixture of ethanol (25 ml) and water (6 ml) was treated with concentrated hydrochloric acid (3 drops) and iron powder (1.14 grams, 20 mmole) at reflux. After 2 hours the cooled mixture was filtered through diatomaceous earth. The filtrate was concentrated and the residue chromatographed (ethyl acetate) to give 444 mg (53%) of 2-[(4-Aminobenzyl) methoxyphosphinoylmethyl]-4-methylpentanoic acid benzyl ester as a yellow oil.

Workup

  1. temperatureat reflux
  2. filtrationAfter 2 hours the cooled mixture was filtered through diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. customthe residue chromatographed (ethyl acetate)

Sources & evidence

ORD record
ord-9dfc9d8faf774ae08320045366240111
Source dataset
uspto-grants-2000_11
Patent number
US06147061

Reaction notes

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