Triethylamine → HCID 54067980, compound

HRID 2295102Notes

Reaction equation

HRID 2295102 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:31][OH:32].C(N(CC)CC)C>C1(C)C=CC=CC=1.ClCCl.CN(C)C=O>[OH:32][NH:31][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:8]=2)=[CH:16][CH:17]=1)=[O:23]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 10805061HCID 10805061, compound

Product 1

HCID 54067980HCID 54067980, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3'-cyclopentyloxy-4'-methoxy-biphenyl-4-carboxylic acid (0.5 g, 1.602 mmol) in toluene (30 mL) was treated with a 2M solution of oxalyl chloride (0.840 mL, 1.68 mmol) in dichloromethane and 1 drop of dimethyl formamide was added. This mixture was heated to reflux for ten minutes, cooled and concentrated in vacuo to an oil. This oil is dissolved in dichloromethane and added dropwise to a mixture of hydroxylamine hydrochloride (0.139 g, 1.25 eq) and triethylamine (0.405 g, 2.5 eq) in dichloromethane (10 mL). After about thirty minutes the reaction the reaction appears to go no further, some of the starting acid remains (by tlc). The reaction is washed with water dried and concentrated. The material is purified via reversed phase HPLC, using a Dynamax-60A Phenyl column wand 70% acetonitrile/water as carrier. This provided the title compound in 9% yield as a crystalline solid (CH2Cl2). mp 181°-183° C.

Workup

  1. additionwas added
  2. temperatureThis mixture was heated
  3. temperatureto reflux for ten minutes
  4. temperaturecooled
  5. concentrationconcentrated in vacuo to an oil
  6. dissolutionThis oil is dissolved in dichloromethane
  7. customAfter about thirty minutes the reaction the reaction
  8. washThe reaction is washed with water
  9. customdried
  10. concentrationconcentrated
  11. customThe material is purified via reversed phase HPLC

Sources & evidence

ORD record
ord-1f52845e81e149c7be0acc963ee2ddd5
Source dataset
uspto-grants-1997_11
Patent number
US05691376

Reaction notes

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