Dimethylcarbamoyl Chloride → HCID 71512084, compound

HRID 1914490Notes

Reaction equation

HRID 1914490 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH2:6][C@H:7]1[CH2:11][O:10][C:9](=[O:12])[C@@H:8]1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([O:21][CH3:22])[CH:15]=1.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31].[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:28][N:29]([CH3:33])[C:30](=[O:31])[O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C@@H:8]2[C@@H:7]([CH2:6][C:5]3[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:11][O:10][C:9]2=[O:12])=[CH:15][C:16]=1[O:21][CH3:22]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 25517Ammonium ChlorideHCID 64981(-)-Arctigenin

Product 1

HCID 71512084HCID 71512084, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R,4R)-4-(3,4-dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one (150 mg, 0.40 mmol, 1.0 eq) in DCM (15 mL) was added TEA (81 mg, 0.81 mmol, 2.0 eq) and DMAP (98 mg, 0.81 mmol, 2.0 eq), followed by N,N-dimethylcarbamoyl chloride (65 mg, 0.60 mmol, 1.5 eq). The mixture was stirred at rt for overnight, then sat. aq. NH4Cl (30 mL) was added. The reaction mixture was extracted with DCM (30 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=1/1, v/v) to afford 4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl dimethylcarbamate (110 mg, 61.6%). LRMS (M+H+) m/z calculated 444.2, found 443.9. 1H NMR (CDCl3, 400 MHz) δ 6.97 (d, 1H), 6.73-6.78 (m, 2H), 6.64-6.70 (m, 1H), 6.50-6.55 (m, 2H), 4.12-4.17 (m, 1H), 3.82-3.90 (m, 1H), 3.85 (s, 3H), 3.83 (s, 3H), 3.77 (s, 3H), 3.11 (s, 3H), 3.00 (s, 3H), 2.97 (d, 2H), 2.49-2.69 (m, 4H).

Workup

  1. extractionThe reaction mixture was extracted with DCM (30 mL×3)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash column chromatography (PE/EA=1/1

Sources & evidence

ORD record
ord-cd9b6adb8b85419d8e4a66fcf8d191e6
Source dataset
uspto-grants-2013_12
Patent number
US08614211B2

Reaction notes

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