1,2-Dichloroethane → HCID 178489970, compound

HRID 1453219Notes

Reaction equation

HRID 1453219 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[O:24][CH3:25])[O:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:33][C:34]1[CH:38]=[C:37]([CH2:39][C:40](O)=[O:41])[O:36][N:35]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[O:24][CH3:25])[O:11][C:10](=[O:12])[C:9]([C:40](=[O:41])[CH2:39][C:37]3[O:36][N:35]=[C:34]([CH3:33])[CH:38]=3)=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acidHCID 167287006-Cyclopentyl-6-[2-(2,4-dimethoxyphenyl)ethyl]tetrahydropyran-2,4-dione

Product 1

HCID 178489970HCID 178489970, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-cyclopentyl-6-[2-(2,4-dimethoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione (52 mg, 0.15 mmol) from Step 2 below, triethylamine (0.075 mL, 0.68 mmol) and (3-Methyl-isoxazol-5-yl)-acetic acid (0.027 g, 0.196 mmol) in CH2Cl2 (1.5 mL) were added DMAP (1 mg), and EDC (37 mg, 0.196 mmol). The reaction was stirred at room temperature for 18 hours, and then diluted with CH2Cl2. The organic was washed with water, and the layers were separated. The organic layer was dried under vacuum, and then purified by preparatory HPLC to give the desired compound (26.2 mg, 37% yield). 1H NMR (CDCl3) δ: 1.47-1.75 (m, 8H), 1.85-1.91 (m, 2H), 2.21 (s, 3H), 2.26-2.32 (m, 1H), 2.48-2.53 (m, 2H), 2.71 (d, J=18.09 Hz, 1H), 2.86 (d, J=18.09 Hz, 1H), 3.69 (s, 3H), 3.71 (s, 3H), 4.40-4.57 (m, 2H), 6.00 (s, 1H), 6.31-6.36 (m, 2H), 6.91 (d, J=7.91 Hz, 1H).

Workup

  1. washThe organic was washed with water
  2. customthe layers were separated
  3. customThe organic layer was dried under vacuum
  4. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-0a26c50352ba4c36a7fa96d0d139c407
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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