Phosphoric Acid → HCID 14520033, compound

HRID 1607772Notes

Reaction equation

HRID 1607772 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[C:10]([C:30]([F:33])([F:32])[F:31])=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19](O)=[O:20])=[C:14]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:13]=[CH:12]2.Cl.[CH3:35][O:36][C:37](=[O:41])[CH2:38][NH:39][CH3:40].C(N(CC)CC)C.OP(O)(O)=O>C(Cl)Cl>[CH3:35][O:36][C:37](=[O:41])[CH2:38][N:39]([C:19]([C:15]1[C:16]2[C:11](=[C:10]([C:30]([F:33])([F:31])[F:32])[C:9]([O:8][CH3:7])=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])[CH3:40]

Participants

7

Reactant 5

HCID 1004Phosphoric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 14520032HCID 14520032, compound

Product 1

HCID 14520033HCID 14520033, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of oxalyl chloride (0.51 mL, 5.8 mmol) in CH2Cl2 (6 mL) was added dropwise to a suspension of 6-methoxy-2-(phenylmethoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid (2.00 g, 5.3 mmol, described in Example 8) in 50 mL of CH2Cl2 under a nitrogen atmosphere. The suspension became homogeneous upon stirring for 1.5 hours. The mixture was then placed under mild vacuum for about 5 minutes to remove the dissolved gases and then was transfered via syringe to a flask containing a suspension of N-methylglycine methyl ester hydrochloride (11.1 g, 8.0 mmol) and triethylamine (3.7 mL, 27 mmol) in 50 mL of CH2Cl2. The suspension was stirred for 20 hours then was poured into additional CH2Cl2 and 1M H3PO4. The organic phase was separated and washed successively with 1M H3PO4, water, saturated NaCl and then dried over Na2SO4. After filtration, concentration and silica gel chromatography with 20:1 CH2Cl2 :ethyl acetate as eluent, the residue was recrystallized from ethanol to give 1.51 g (62% yield) of the title compound as a white powder, m.p. 95°-98° C.

Workup

  1. waitThe mixture was then placed under mild vacuum for about 5 minutes
  2. customto remove the dissolved gases
  3. customwas transfered via syringe to a flask
  4. additioncontaining
  5. stirringThe suspension was stirred for 20 hours
  6. customThe organic phase was separated
  7. washwashed successively with 1M H3PO4, water, saturated NaCl
  8. dry with materialdried over Na2SO4
  9. filtrationAfter filtration, concentration and silica gel chromatography with 20:1 CH2Cl2
  10. customethyl acetate as eluent, the residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5a92f8a3542842fe8bc8a0acabd52aab
Source dataset
uspto-grants-1989_09
Patent number
US04866197

Reaction notes

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