Hydrochloric Acid → HCID 71536237, compound

HRID 1473251Notes

Reaction equation

[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[S:19][C:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:13]=2[C:12]=1[C:26]1[C:27]([CH3:36])=[C:28]2[C:33](=[CH:34][CH:35]=1)[O:32][CH2:31][CH2:30][CH2:29]2)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[S:19][C:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:13]=2[C:12]=1[C:26]1[C:27]([CH3:36])=[C:28]2[C:33](=[CH:34][CH:35]=1)[O:32][CH2:31][CH2:30][CH2:29]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of compound methyl 2-(tert-butoxy)-2-(2-methyl-4-(5-methylchroman-6-yl)-1-oxo-1,2,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-c]pyridin-3-yl)acetate (20 mg, 0.04 mmol) in Tetrahydrofuran (THF) (3 mL) and Water (3 mL) was added lithium hydroxide hydrate (20 mg, 0.48 mmol). The mixture was stirred at 65° C. for overnight. The reaction was cooled to room temperature, and solvent was removed by concentrated under reduced pressure to afford an oil, which was acidified with 1N aqueous HCl to pH=3, the resulting precipitate was collected by filtration to afford title product (11.5 mg, 59% yield) as white solid. 1H NMR: (Methanol-d4, 400 MHz) δ 0.99, 1.15 (s, total, 9H), 1.35˜1.52 (m, 2H), 1.69˜1.72 (m, 4H), 1.86 (s, 3H), 2.08˜2.11 (m, 2H), 2.65˜2.75 (m, 2H), 2.85˜2.89 (m, 2H), 3.77, 3.80 (s, total, 3H), 6.72˜6.78 (m, 1H), 6.98˜7.27 (m, 1H). LCMS (m/z) ES+=496 (M+1).

Workup

temperatureThe reaction was cooled to room temperature
customsolvent was removed
concentrationby concentrated under reduced pressure
customto afford an oil, which
filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-932c5da4889144c4a402ba29717b25e4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012642B2

Reaction notes

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