Triethylamine → HCID 53961439, compound

HRID 1637122Notes

Reaction equation

HRID 1637122 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16][C:17]([OH:19])=O)[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.[NH2:34][CH2:35][CH:36](O)[CH2:37][CH3:38].C(N(CC)CC)C>CN(C)C=O.ClCCl.O1CCCC1.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH2:16][C:17]3[O:19][C:36]([CH2:37][CH3:38])=[CH:35][N:34]=3)[C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 261071-Amino-2-butanolHCID 65578Oxalyl chlorideHCID 15463366HCID 15463366, compound

Product 1

HCID 53961439HCID 53961439, compoundYield 94.9%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylethynylpropionic acid (0.50 g, 1.37 mmol) and dimethyl formamide (3 drops) in dichloromethane (10 mL) at room temperature under an argon atmosphere was dropwise added oxalyl chloride (0.125 mL, 1.44 mmol). The reaction was stirred 0.5 h, was evaporated, was dissolved in tetrahydrofuran (5 mL) and was added to a solution of 1-amino-2-butanol (0.15 mL, 1.52 mmol) and triethylamine (0.23 mL, 1.64 mmol) in tetrahydrofuran (10 mL) and was stirred at room temperature under an argon atmosphere for 1 h. Water was added, the reaction was extracted with three times dichloromethane, was dried (MgSO4) and was evaporated. Purification by flash chromatography, eluted with 2:98 methanol:dichloromethane provided the title compound (0.54 g, 91%) as a white solid, mp.94-96° C.

Workup

  1. customat room temperature
  2. customwas evaporated
  3. dissolutionwas dissolved in tetrahydrofuran (5 mL)
  4. stirringwas stirred at room temperature under an argon atmosphere for 1 h
  5. extractionthe reaction was extracted with three times dichloromethane
  6. dry with materialwas dried (MgSO4)
  7. customwas evaporated
  8. customPurification by flash chromatography
  9. washeluted with 2:98 methanol

Sources & evidence

ORD record
ord-b584a55a36e94b53b0876d58b76ab6a3
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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