N,N-dimethylhydroxylamine hydrochloride → HCID 18958982, compound

HRID 1708504Notes

Reaction equation

HRID 1708504 reaction equation
C1([CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])CCCCC1.C(N1[CH:41]=[CH:40]N=C1)(N1C=CN=C1)=O.Cl.[CH3:43][N:44]([CH3:46])O>C(Cl)Cl>[CH3:43][N:44]([CH3:46])[O:11][C:9](=[O:10])[C:8]([CH:41]1[CH2:40][CH2:13][CH2:12][CH2:8][CH2:7]1)([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[CH:16][CH:17]=1)[CH3:7]

Participants

5

Reactant 3

HCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 14674838HCID 14674838, compound

Product 1

HCID 18958982HCID 18958982, compoundYield 171.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-propionic acid (389 mg, 1 mmol) in methylene chloride (10 mL) was added 1,1'-carbonyldiimidazole (162 mg, 1 mmol). The mixture was stirred at ambient temperature for 15 minutes and then N,N-dimethylhydroxylamine hydrochloride (147 mg, 1.5 mmol) was added. The resulting mixture was stirred at ambient temperature for an additional 20 minutes and then partitioned between ethyl acetate (50 mL) and saturated NaHCO3 (5 mL). The organic layer was washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification on a silica gel column eluting with 2:1 CH2Cl2 -EtOAc afforded 370 mg (86%) of the title compound. m.p. 98°-99° C. 1H NMR (DMSO-d6, 300 MHz) δ 0.9 (m, 2H), 1.1 (m, 4H), 1.63 (m, 6H), 1.8 m (m, 1H), 2.6 (s, 6H), 3.7 (t, J=7Hz, 1H), 5.35 (s, 2H), 7.04 (d, J=9Hz, 2H), 7.23 (d, J=9Hz, 2H), 7.62 (m, 1H), 7.68 (d, J =8Hz, 1H), 7.8 (m, 1H), 8.0 (t, J=8Hz, 2H), 8.42 (d, J=8Hz, 1H). IR (CDCl3): 1750,1600 cm-1. MS (DCI/NH3) m/e 433 (M+H)+. Analysis calcd for C27H32N2O3 : C, 74.97; H, 7.46; N, 6.48. Found: C, 74.81; H, 7.47; N, 6.41.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for an additional 20 minutes
  2. custompartitioned between ethyl acetate (50 mL) and saturated NaHCO3 (5 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification on a silica gel column
  7. washeluting with 2:1 CH2Cl2 -EtOAc

Sources & evidence

ORD record
ord-b21925c3ac834a60a5dd8cb1b2ceb2a5
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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