Dimethylcarbamoyl Chloride → HCID 71512084, 화합물

HRID 1914490노트

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HRID 1914490 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 71512084HCID 71512084, 화합물수율 62%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cd9b6adb8b85419d8e4a66fcf8d191e6
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614211B2

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