Triethylamine → HCID 10667946, compound

HRID 1385523Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH2:18][O:19][CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH:10]([CH2:21][OH:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH2:18][O:19][CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH:10]([CH2:21][O:22][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 17 (80 mg, 0.26 mmol) in 5 mL anhydrous CH2Cl2 was cooled to 0° C. and treated with Et3N (79 μL, 0.57 mmol). After 10 min, MsCl (40 μL, 0.52 mmol) was added and the reaction mixture was subsequently warmed to 25° C. and stirred for 3 h. The reaction solution was concentrated under reduced pressure. Flash chromatography (SiO2, 2.5×10 cm, 30% EtOAc/hexane) yielded pure 18 (94 mg, 94%) as a colorless oil: 1H NMR (CDCl3, 250 MHz) δ7.49 (m, 1H), 7.15 (m, 1H), 6.68 (d, J=9.0 Hz, 1H), 5.19 (d, J=8.8 Hz, 1H), 5.17 (d, J=8.8 Hz, 1H), 4.58 (dd, J=3.6, 9.7 Hz, 1H), 4.21 (app t, J=8.9 Hz, 1H), 4.00 (m, 2H), 3.79 (m, 1H), 3.46 (s, 3H), 2,71 (s, 3H), 1.54 (s, 9H);13C NMR (CDCl3, 100 MHz) δ153.9, 152.1, 130.5, 110.2, 108.8, 107.7, 103.9, 94.4, 81.0, 69.9, 56.2, 51.1, 37.9, 37.2, 28.2; IR (film) νmax 2976, 1703, 1610, 1479, 1463, 1391, 1355, 1254, 1175, 1154, 1061, 952 cm−1; FABHRMS (NBA/CsI) m/z 520.0388 (C17H25NO7S+Cs+ requires 520.0406).

Workup

concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-4cb6ed5789b74b96a69f7666a2ddc3a0
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262271B1

Reaction notes

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