Hydroxyamine hydrochloride → HCID 54057987, compound

HRID 2209726Notes

Reaction equation

HRID 2209726 reaction equation
[C:1]([C:3]1[CH:37]=[CH:36][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:27]([N:29]([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])=[O:28])=[C:18]([CH:26]=2)[O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:39][OH:40].[O-]CC.[Na+]>C(O)C>[NH2:2][C:1](=[N:39][OH:40])[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:27](=[O:28])[N:29]([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:31])[CH3:32])=[C:18]([CH:26]=2)[O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 19040982HCID 19040982, compound

Product 1

HCID 54057987HCID 54057987, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred solution of ethyl 5-[5-(4-cyanophenoxy)pentyloxy]-2-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxyacetate (970 mg, 1.9 mmol) in 20 mL of anhydrous ethanol is treated with hydroxylamine hydrochloride (400 mg, 5.7 mmol) and 21% sodium ethoxide solution in ethanol (2.1 mL, 5.7 mmol) and stiffed at 50° C. overnight. The reaction is concentrated in vacuo and purified by chromatography on silica gel (20 g) with 80-100% ethyl acetate/hexane followed by 0-10% methanol/ethyl acetate as the eluent to afford (a) ethyl 2-[5-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxy]acetate as a colorless foam;

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. custompurified by chromatography on silica gel (20 g) with 80-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-275b19d003c84866af4ec4ada5ed25f3
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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