Triethylamine → 5-(2-Diazo-acetyl)-biphenyl-3-carboxylic acid propylamide

HRID 2421621Notes

Reaction equation

HRID 2421621 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:8]=[C:9]([C:19]([OH:21])=O)[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)=[O:6])[CH2:2][CH3:3].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.C[Si]([CH:39]=[N+:40]=[N-:41])(C)C>C1(C)C=CC=CC=1.CCOCC.CN(C=O)C>[CH2:1]([NH:4][C:5]([C:7]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]=[C:9]([C:19](=[O:21])[CH:39]=[N+:40]=[N-:41])[CH:8]=1)=[O:6])[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 167693TrimethylsilyldiazomethaneHCID 672136885-Propylcarbamoyl-biphenyl-3-carboxylic acid

Product 1

HCID 860888475-(2-Diazo-acetyl)-biphenyl-3-carboxylic acid propylamide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

68E (194 mg, 0.69 mmol) was suspended in 1.5 mL of toluene with 11 μL of dry DMF. Oxalyl chloride (72 μL, 0.82 mmol) was then added dropwise at 0° C. leading to a gas evolution. After the addition, the reaction was stirred at room temperature for 2 hours. After that time, the reaction mixture was concentrated. The residue was dissolved in THF. At 0° C., triethylamine (95 μL, 0.69 mmol) was added followed by trimethylsilyldiazomethane (582 μL of a 2 M solution in Et2O). The reaction was then stirred at room temperature for 16 hours. The reaction mixture was then concentrated and the residue was purified using SiO2 with CH2Cl2/AcOEt 98:2 to 85:15. An orange oil was obtained (100 mg, 48%). NMR 1H (ppm, CDCl3): 8.14 (t., J4=1.68 Hz, 1H), 8.06 (t., J4=1.60 Hz, 1H), 8.03 (t., J4=1.68 Hz, 1H), 7.59-7.55 (m, 2H), 7.46-7.34 (m, 3H), 6.51 (br.s., 1H), 6.01 (s, 1H), 3.46-3.39 (m, 2H), 1.64 (sext., J3=7.24 Hz, 2H), 0.97 (t., J3=7.37 Hz, 3H).

Workup

  1. additionAfter the addition
  2. concentrationAfter that time, the reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in THF
  4. stirringThe reaction was then stirred at room temperature for 16 hours
  5. concentrationThe reaction mixture was then concentrated
  6. customthe residue was purified
  7. customAn orange oil was obtained (100 mg, 48%)

Sources & evidence

ORD record
ord-9f19b2a99b034637b6b5ea881c53e5a5
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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