HCID 21185183, compound → HCID 21185184, compound

HRID 1385516Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([O:21]COC)[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[CH:15]=2)[CH:10]([CH2:25][Cl:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)C.C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([OH:21])[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[CH:15]=2)[CH:10]([CH2:25][Cl:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 28 (18 mg, 47.5 μmol) in 1.5 mL of 1:1 i-PrOH/THF was treated with 12 N HCI (0.20 mL, 0.38 mmol) and the mixture was stirred at 25° C. for 6 h before the volatiles were removed in vacuo. Flash chromatography (SiO2, 1.5×15 cm, 0-20% EtOAc/hexane gradient) provided 30 (14.5 mg, 90%) as a pale yellow oil: 1H NMR (CDCl3, 250 MHz) δ7.85 (d, J=8.0 Hz, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.43-7.30 (m, 2H), 5.67 (s, 1H), 4.09-3.86 (m, 4H), 3.65 (dd, J=8.0, 10.0 Hz, 1H), 1.59 (s, 9H);13C NMR (CDCl3, 6.25 MHz) δ147.9, 135.8, 132.7, 128.8, 128.0, 126.6, 123.7, 121.2, 119.5, 119.5, 104.4, 77.2, 52.6, 46.4, 34.7, 28.5; IR (film) νmax3368, 2976, 1668, 1477, 1450, 1369, 1145, 978, 746 cm−1; FABHRMS (NBA/CsI) m/z 466.0197 (C18H20CINO3+Cs+requires 466.0186). (−)-(3S)-30: [α]D25 −54 (c 0.25, CH3OH); (+)-(3R)-30: [α]D25+51 (c 0.30, CH3OH).

Workup

customwere removed in vacuo

Sources & evidence

ORD record: ord-f29dc2b8f4bd402da804182a128e1ee6
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262271B1

Reaction notes

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