Carbon Tetrachloride → HCID 21185183, compound

HRID 1385515Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([O:21][CH2:22][O:23][CH3:24])[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[CH:15]=2)[CH:10]([CH2:25]O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)(Cl)[Cl:28].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([O:21][CH2:22][O:23][CH3:24])[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[CH:15]=2)[CH:10]([CH2:25][Cl:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

From 27: A solution of 27 (55 mg, 0.16 mmol) in 3 mL anhydrous CH2Cl2 was treated with CCl4 (155 μL, 1.6 mmol) and Ph3P (212 mg, 0.81 mmol) and the mixture was stirred at 25° C. for 2 h. The solution was concentrated in vacuo. Flash chromatography (SiO2, 1.5×15 cm, 0-12% EtOAc/hexane gradient) provided 28 (52 mg, 90%) as a white solid: mp 99-101° C.; 1H NMR (CDCl3, 250 MHz) δ8.03 (br s, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H), 7.37 (m, 2H), 5.24 (d, J=6.1 Hz, 1H), 5.15 (d, J=6.1 Hz, 1H), 4.06 (m, 4H), 3.65 (s, 3H), 3.51 (app t, J=10.1 Hz, 1H), 1.59 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ152.3, 150.5, 141.1, 136.2, 127.9, 126.6, 124.6, 124.1, 122.4, 121.4, 107.7, 100.0, 81.2, 57.5, 52.1, 45.9, 40.8, 28.4; IR (film) νmax 2976, 1704, 1634, 1449, 1336, 1147, 1055, 983 cm−1; FABHRMS (NBA) m/z 378.1463 (C20H24ClNO4+H+ requires 378.1472).

Workup

concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-3641e543041d4135a59e24a14e281081
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262271B1

Reaction notes

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