Triethylamine → HCID 18409288, compound

HRID 993470Notes

Reaction equation

HRID 993470 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]2([C:49]([NH:51][CH2:52][CH2:53][CH3:54])=[O:50])[C:48]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:42]3[C:37]2=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:28][CH:27]=1)([O-])=O.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:23][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]2([C:49]([NH:51][CH2:52][CH2:53][CH3:54])=[O:50])[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=3[C:43]3[C:48]2=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:28][CH:27]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 752372-Phenoxybenzoic acidHCID 18409330HCID 18409330, compound

Product 1

HCID 18409288HCID 18409288, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 2-phenoxybenzoic acid (Aldrich Chemical Co.) (111 mg, 0.518 mmol) and DMF (2 drops) in CH2Cl2 (1.5 mL) was added oxalyl chloride (389 μL, 2.0M in CH2Cl2, 0.777 mmol). The reaction bubbled for 10 min, then was stirred at RT under argon for 1.5 h. The reaction was concentrated in vacuo, and the resulting residue was dissolved in CH2Cl2 (1.5 mL) and added dropwise to a solution of Example 204 Part A compound (172 mg, 0.432 mmol) and triethylamine (90 μL, 0.648 mmol) in CH2Cl2 (1.5 mL) at 0° C. under argon. The reaction was stirred at 0° C. for 10 min, diluted with CH2Cl2 (20 mL), washed with saturated NaHCO3 (5 mL) and brine (5 mL), then dried over Na2SO4. Evaporation gave a yellow oil, which was dissolved in a minimum amount of CH2Cl2 and purified by flash chromatography on silica gel (50 g) eluting with 30% EtOAc/hexane to provide title compound (211 mg, 82%) as a yellow gum.

Workup

  1. customThe reaction bubbled for 10 min
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in CH2Cl2 (1.5 mL)
  4. stirringThe reaction was stirred at 0° C. for 10 min
  5. washwashed with saturated NaHCO3 (5 mL) and brine (5 mL)
  6. dry with materialdried over Na2SO4
  7. customEvaporation
  8. customgave a yellow oil, which
  9. custompurified by flash chromatography on silica gel (50 g)
  10. washeluting with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-f0de375b62de4ad780c286df192d0db5
Source dataset
uspto-grants-2002_10
Patent number
US06472414B1

Reaction notes

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