Hydrochloric Acid → HCID 70562350, compound

HRID 1427316Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([N:26](COCC[Si](C)(C)C)[S:27]([CH3:30])(=[O:29])=[O:28])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)([CH2:11][CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:9][CH3:10])=[CH:4][CH:3]=1.Cl>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)([CH2:11][CH2:12][C:13]([F:16])([F:14])[F:15])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the product from step C (20 mg, 0.034 mmol, enantiomer A), 2 M HCl (1 mL) and EtOH (2 mL) was heated to 50° C. for 3 h. The volatile was removed under reduced pressure. The residue was purified by Combiflash (mobile phase: MeOH/water (0.08% of NH4HCO3)) to give the title compound. LC/MS m/z=458.7 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=3.6 Hz, 1H), 7.29 (d, J=8.4 Hz, 2H), 7.10 (d, J=7.6 Hz, 1H), 7.05 (d, J=8.8 Hz, 2H), 6.86 (t, J=8.1 Hz, 1H), 6.59-6.58 (m, 2H), 6.40 (d, J=8.4 Hz, 1H), 3.03 (s, 3H), 2.74-2.67 (m, 1H), 2.55-2.45 (m, 2H), 2.26-2.16 (m, 1H), 1.89-1.86 (m, 1H), 1.45-1.38 (m, 1H), 0.67 (t, J=7.2 Hz, 3H).

Workup

customThe volatile was removed under reduced pressure
customThe residue was purified by Combiflash (mobile phase: MeOH/water (0.08% of NH4HCO3))

Sources & evidence

ORD record: ord-35ae0d433b1c4fe4afdbdb8793d6dd63
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933113B2

Reaction notes

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