Hydroxyamine hydrochloride → HCID 54386776, compound

HRID 2209728Notes

Reaction equation

[C:1]([C:3]1[CH:39]=[CH:38][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:29]([N:31]([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])=[O:30])=[C:18]([CH:28]=2)[O:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:41][OH:42].[O-]CC.[Na+]>C(O)C>[NH2:2][C:1](=[N:41][OH:42])[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:29](=[O:30])[N:31]([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:33])[CH3:34])=[C:18]([CH:28]=2)[O:19][C:20]([CH3:26])([CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A stirred solution of ethyl 2-[5-[5-(4-cyanophenoxy)pentyloxy]-2-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]-2-methylpropanoate (1.2 g, 2.3 mmol) in 30 mL of anhydrous ethanol is treated with hydroxylamine hydrochloride (480 mg, 6.8 mmol) and 21% sodium ethoxide solution in ethanol (2.6 mL, 6.8 mmol) and stirred at 50° C. overnight. The reaction is concentrated in vacuo and purified by chromatography on silica gel (20 g) with 80% ethyl acetate/hexane as the eluent to afford ethyl 2-[5-[5-[4-[amino(hydroxyimino)methyl]-phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxy]-2-methylpropanoate as a colorless foam;

Workup

concentrationThe reaction is concentrated in vacuo
custompurified by chromatography on silica gel (20 g) with 80% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record: ord-695e11e5727b480f9113b47ee747ec6d
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455274

Reaction notes

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