Triethylamine → HCID 86666324, compound

HRID 1026351Notes

Reaction equation

HRID 1026351 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.CN([C:16]([O:20][N:21]1N=NC2C=CC=N[C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CNOC>ClCCl.O>[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([N:21]([O:20][CH3:16])[CH3:22])=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24721648(2-Bromo-4-hydroxyphenyl)acetic acid

Product 1

HCID 86666324HCID 86666324, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2-bromo-4-hydroxyphenyl)acetic acid (0.67 g), HATU (1.33 g), triethylamine (0.35 g) and N,O-dimethylhydroxylamine hydrochloride (0.34 g) in dichloromethane (30 mL) was stirred overnight, to which water (30 mL) was added. The organic layer was separated. The water layer was extracted by ethyl acetate (20 mL×3). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to afford the title compound (773 mg).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionThe water layer was extracted by ethyl acetate (20 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-f36d87ca33eb4713bd402beb990bfd1d
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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