Triethylamine → HCID 14520026, compound

HRID 1607767Notes

Reaction equation

HRID 1607767 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1[C:21]([OH:23])=O.C(N(CC)CC)C.Cl.[CH3:32][O:33][C:34](=[O:38])[CH2:35][NH:36][CH3:37]>C(Cl)Cl.CN(C)C=O.O>[CH3:32][O:33][C:34](=[O:38])[CH2:35][N:36]([C:21]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[O:8][CH3:7])=[O:23])[CH3:37]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 14520025HCID 14520025, compound

Product 1

HCID 14520026HCID 14520026, compoundYield 79.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalyl chloride (0.95 mL, 11 mmol) in CH2Cl2 (10 mL) was added to a suspension of 2,6-dimethoxy-1-naphthalenecarboxylic acid (2.32 g, 10 mmol, described in Example 1) and N,N-dimethylformamide (2 drops, catalyst) in CH2Cl2 (50 mL) under nitrogen. After 1.5 hours, triethylamine (5 mL, 36 mmol) and N-methylglycine methyl ester hydrochloride (2.1 g, 15 mmol) were added. The resulting mixture was stirred at room temperature overnight and then poured into water (200 mL) and CH2Cl2 (200 mL). The aqueous phase was washed with CH2Cl2 (100 mL) and the combined CH2Cl2 phases were washed successively with 1M H3PO4 (2 x 100 mL), water (100 mL), saturated NaHCO3 (50 mL), brine (100 mL) and dried over Na2SO4. Filtration and concentration left a pale brown foam which was filtered through a short column of silica gel with 1:1 ethyl acetate:hexane to obtain 2.53 g of the title compound as a pale yellow oil. NMR (200 MHz, CDCl3): δ2.87, 3.30 (2s, 3:1 ratio, 3H), 3.57-4.0 (m, 10H), 4.99 (d, 1H, J=17 Hz), 7.05-7.3 (m, 3H), 7.6-7.9 (m, 2H);

Workup

  1. washThe aqueous phase was washed with CH2Cl2 (100 mL)
  2. washthe combined CH2Cl2 phases were washed successively with 1M H3PO4 (2 x 100 mL), water (100 mL), saturated NaHCO3 (50 mL), brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and concentration
  5. waitleft a pale brown foam which
  6. filtrationwas filtered through a short column of silica gel with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-d5fba9b0aed54691bd7215068c910740
Source dataset
uspto-grants-1989_09
Patent number
US04866197

Reaction notes

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