Triethylamine → HCID 76528170, compound

HRID 84194Notes

Reaction equation

HRID 84194 reaction equation
[NH2:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4]1.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](/[CH:18]=[CH:19]/[C:20](O)=[O:21])=[CH:10]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C1COCC1>[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=[CH:19][C:20]([NH:1][O:2][CH:3]2[CH2:8][CH2:7][CH2:6][CH2:5][O:4]2)=[O:21])=[CH:10]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 53750483-Indoleacrylic acid

Product 1

HCID 76528170HCID 76528170, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NH2OTHP (0.38 g, 3.21 mmol) was added to a solution of trans-3-indoleacrylic acid (17) (0.50 g, 2.67 mmol), PyBOP (1.47 g, 2.83 mmol), triethylamine (0.74 ml, 6.41 mmol) in THF (25 mL). The mixture was stirred at room temperature for 2 h and then was concentrated under reduced pressure. The residue was dissolved in EtOAc and quenched with water, followed by extraction with EtOAc (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc:n-hexane=1.5:1:1% NH3(aq)) to afford 18. 1H NMR (500 MHz, CD3OD): δ 1.58-1.70 (m, 3H), 1.79-1.90 (m, 3H), 3.63-3.65 (m, 1H), 4.03-4.08 (m, 1H), 4.97-4.98 (m, 1H), 6.47 (d, J=14.9 Hz, 1H), 7.15-7.21 (m, 2H), 7.41 (d, J=7.8 Hz, 1H), 7.59 (s, 1H), 7.84-7.87 (m, 2H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. customquenched with water
  4. extractionfollowed by extraction with EtOAc (20 mL×3)
  5. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (EtOAc:n-hexane=1.5:1:1% NH3(aq))

Sources & evidence

ORD record
ord-8448e54082284f0f8ec25d965c9c1b67
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

Loading…