Triethylamine → (RS)-ethoxy-(2-oxo-3-phenylamino-2H-pyridin-1-yl)-acetic acid ethyl ester

HRID 1828096Notes

Reaction equation

HRID 1828096 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:17]([O:19][C:20](=[O:33])[CH:21]([N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[C:26]1=[O:32])[O:22][CH2:23][CH3:24])[CH3:18].CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl>[CH2:17]([O:19][C:20](=[O:33])[CH:21]([O:22][CH2:23][CH3:24])[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:26]1=[O:32])[CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 2724126TempoHCID 69641593(RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester

Product 1

HCID 69641585(RS)-ethoxy-(2-oxo-3-phenylamino-2H-pyridin-1-yl)-acetic acid ethyl esterYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 ml flask was added in sequence molecular sieves 4Å(200 mg), phenylboronic acid (418 mg), CH2Cl2 (10 ml), triethylamine (0.48 ml), a solution of (RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester (412 mg, example 19.2) in CH2Cl2 (10 ml), cupric acetate (31 mg) and TEMPO (295 mg). A CaCl2 trap was placed over the flask. The reaction was then stirred under air for 3 days. The solids were filtered off and washed with CH2Cl2. The filtrate was concentrated. The crude product was purified by chromatography (silica gel, gradient cyclohexane/EtOAc) to give (RS)-ethoxy-(2-oxo-3-phenylamino-2H-pyridin-1-yl)-acetic acid ethyl ester (258 mg) as green oil. MS 317.2 ([M+H]+)

Workup

  1. customA CaCl2 trap was placed over the flask
  2. filtrationThe solids were filtered off
  3. washwashed with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was purified by chromatography (silica gel, gradient cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-7ae369e00fda4909827498ee2a511184
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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