Diisopropylethylamine → HCID 44539799, compound

HRID 402578Notes

Reaction equation

HRID 402578 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)C(C)C)(C)C.[F:13][C:14]1[CH:34]=[CH:33][C:17]([O:18][CH2:19][C:20]2[C:21]([CH2:31][OH:32])=[C:22]([OH:30])[C:23]([C:26](OC)=[O:27])=[N:24][CH:25]=2)=[CH:16][CH:15]=1>CO.CCOC(C)=O>[OH:3][NH:2][C:26]([C:23]1[C:22]([OH:30])=[C:21]([CH2:31][OH:32])[C:20]([CH2:19][O:18][C:17]2[CH:33]=[CH:34][C:14]([F:13])=[CH:15][CH:16]=2)=[CH:25][N:24]=1)=[O:27]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 44540665HCID 44540665, compound

Product 1

HCID 44539799HCID 44539799, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Hydroxylamine hydrochloride (0.045 g, 0.65 mmol) and N,N-diisopropylethylamine (0.14 mL, 0.81 mmol) were added to a solution of methyl 5-((4-fluorophenoxy)methyl)-3-hydroxy-4-(hydroxymethyl)picolinate 28b (0.050 g, 0.16 mmol) in MeOH (3 mL) and heated to 70° C. for 5 h. The crude mixture was diluted with EtOAc and washed with saturated aqueous ammonium chloride solution and brine. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (0.048 g, 96%): LC-MS (M+H)+ m/z 309.

Workup

  1. washwashed with saturated aqueous ammonium chloride solution and brine
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0be874bc052d4c5bb8400debf0550ec0
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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