Hydroxyamine hydrochloride → HCID 42599707, compound

HRID 1362572Notes

Reaction equation

HRID 1362572 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:20])[CH2:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[NH2:23][OH:24].C[O-].[Na+]>CO>[OH:24][NH:23][C:3](=[O:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:20])[CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 66958417HCID 66958417, compound

Product 1

HCID 42599707HCID 42599707, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(Method J7) To a mixture of 6-(4-phenyl-but-3-enoylamino)-hexanoic acid methyl ester (3/57) (100 mg, 0.35 mmol) and hydroxylamine hydrochloride (96 mg, 1.38 mmol) in methanol (1 ml) the 3.43 N solution of sodium methylate (0.61 ml, 2.1 mmol) in methanol was added. The mixture was stirred for 1 hour at room temperature, diluted with saturated NaH2PO4 (10 ml), and extracted with ethyl acetate (2×20 ml). The organic extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated and the residue was crystallized from ethyl acetate to give the title product, yield 66%. M.p. 127-128° C. (from ethyl acetate). 1H NMR (DMSO-d6, HMDSO), δ: 1.07-1.68 (m, 6H); 1.78-2.06 (m, 2H); 2.03 (t, 2H, J=6.6 Hz); 2.85-3.18 (m, 4H); 6.30 (dd, 1H, J=16.1 and 6.0 Hz); 6.48 (d, 1H, J=16.1 Hz); 7.14-7.53 (m, 5H); 7.85 (t, 1H, J=5.8 Hz); 8.63 (br s, 1H); 10.32 (br s, 1H). HPLC analysis on Zorbax SB-C18 column: impurities 2% (column size 4.6×150 mm; mobile phase 0.1% H3PO4, gradient from 50:50 to 90:10; detector UV 254 nm; sample concentration 0.75 mg/ml, flow rate 1.5 ml/min). Anal. Calcd for C16H22N2O3: C, 66.19; H, 7.64; N, 9.65. Found: C, 66.19; H, 7.69; N, 9.67.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-eb809638b3bb49298ad14dc61cc2386a
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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