Pyridine → HCID 19894147, compound

HRID 892860Notes

Reaction equation

HRID 892860 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[C:9](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.C([O:24][C:25](Cl)=[O:26])C(C)C.[CH2:28](N(CC)CC)C.Cl.[CH3:36][NH:37][O:38][CH3:39].N1[CH:45]=[CH:44][CH:43]=CC=1>C(Cl)Cl.[Cl-].[Na+].O>[CH3:39][O:38][N:37]([CH3:36])[C:15](=[O:17])/[CH:14]=[CH:13]/[C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:28][CH:44]([CH3:43])[CH3:45])=[CH:19][C:18]=2[C:25]([OH:26])=[O:24])[CH:8]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 21684721HCID 21684721, compound

Product 1

HCID 19894147HCID 19894147, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of trans-3-(3-(4-hydroxyphenoxy)phenyl)propenoic acid (26.22 g, 102.4 mmol) in CH2Cl2 (500 mL) at 0° C., was added iso-butylchloroformate (29.38 g, 215.1 mmol) followed by the dropwise addition of triethylamine (21.73 g, 215.1 mmol). Upon completion of addition, the cooling bath was removed and the reaction allowed to warm to r.t. and stirred for 1 hr. N,O-dimethylhydroxylamine hydrochloride (11.99 g, 122.9 mmol) was then added followed by the dropwise addition of pyridine (19.44 g, 245.8 mmol) and the reaction was stirred for 30 mins. It was then diluted with brine (500 mL) and the layers were separated. The aqueous was extracted with CH2Cl2 (2×500 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 1:1) to afford trans-N-methoxy-N-methyl-3-(3-(4-iso-butyloxycarboxyphenoxy)phenyl)propenamide (27.13 g, 66%).

Workup

  1. additionUpon completion of addition
  2. customthe cooling bath was removed
  3. stirringthe reaction was stirred for 30 mins
  4. customthe layers were separated
  5. extractionThe aqueous was extracted with CH2Cl2 (2×500 mL)
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 1:1)

Sources & evidence

ORD record
ord-9953e4b9a074499e86cea848accb0aee
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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