Triethylamine → HCID 56925774, compound

HRID 2175464Notes

Reaction equation

HRID 2175464 reaction equation
[CH3:1][C:2]1([CH3:20])[O:11][C:10]2[C:5](=[N:6][C:7]([CH2:12][NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[C:33](Cl)=[O:34].C(Cl)Cl.CCOC(C)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:20])[O:11][C:10]2[C:5](=[N:6][C:7]([CH2:12][N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:30]([O:29][CH3:28])[CH:31]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 21226138Dichloromethane ethylacetateHCID 56926180HCID 56926180, compound

Product 1

HCID 56925774HCID 56925774, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 25a (60 mg, 0.226 mmol) in DCM (3 mL) was added triethylamine (0.06 mL, 0.452 mmol) and 3,4-dimethoxybenzoyl chloride (54 mg, 0.271 mmol). The reaction was stirred overnight at room temperature. The reaction mixture was washed with dH2O (×2) and sat. NaHCO3 (×2), dried over MgSO4 and concentrated in vacuo. Purification by column: silica gel: 3:1 DCM/EtOAc gave a quantitative yield of a light yellow oil. 1H NMR (CDCl3): δ 7.26-7.17 (m, 3H), 7.17-7.08 (m, 3H), 7.06-6.97 (m, 2H), 6.95 (t, J=5.0 Hz, 1H), 6.66 (d, J=8.4 Hz, 1H), 6.53-6.40 (m, 1H), 5.92-5.79 (m, 1H), 5.16 (s, 2H), 3.83 (s, 3H), 3.66 (s, 3H), 1.46 ppm (s, 6H). 13C NMR (CDCl3): δ 169.9, 150.3, 149.0, 148.6, 147.9, 144.7, 140.6, 135.1, 129.0, 127.8, 127.2, 126.3, 124.0, 123.6, 123.0, 122.3, 112.6, 109.9, 77.4, 77.0, 77.0, 76.7, 55.8, 55.7, 55.6, 28.2 ppm. HRMS (ESI) m/z calcd for C26H27N2O4 [(M+H)+] 431.1971. found: 431.1951.

Workup

  1. washThe reaction mixture was washed with dH2O (×2) and sat. NaHCO3 (×2)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification by column

Sources & evidence

ORD record
ord-374c6b1835cd4950a7a7345039393fb8
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

Loading…