Triethylamine → HCID 20088231, compound

HRID 275491Notes

Reaction equation

HRID 275491 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][NH:17][C:18](=[O:22])[C:19](O)=[O:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:30][OH:31].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O.O.O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][NH:17][C:18]([C:19]([NH:30][OH:31])=[O:20])=[O:22])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 15232861HCID 15232861, compound

Product 1

HCID 20088231HCID 20088231, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]oxamic acid (651 mg, 2.12 mmol) in methylene chloride (5 mL) containing 2 drops of dimethylformamide at 0° C. under an argon atmosphere was added oxalyl chloride (0.39 mL, 4.45 mmol) and the resulting mixture was stirred for 1 h. This was added to a solution of hydroxylamine hydrochloride (591 mg, 8.50 mmol) and triethylamine (1.75 mL, 12.70 mmol) in 1:5 water/tetrahydrofuran (10 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred at 0° C. for 1 hour then allowed to warm to room temperature and stirred an additional 2 h. The mixture was partitioned between water and methylene chloride and the organic extract was dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1:5:94 acetic acid/methanol/methylene chloride, to provide the hydroxy oxamide (489 mg, 72% ): m.p. 136°-137° C.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  2. stirringstirred an additional 2 h
  3. customThe mixture was partitioned between water and methylene chloride
  4. extractionthe organic extract
  5. dry with materialwas dried (potassium carbonate)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with 1:5:94 acetic acid/methanol/methylene chloride

Sources & evidence

ORD record
ord-20258c65b3394f218b336aa783b1b0c1
Source dataset
uspto-grants-1995_02
Patent number
US05393788

Reaction notes

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