Hydrochloric Acid → HCID 118274423, compound

HRID 522238Notes

Reaction equation

[F:1][C:2]1[CH:37]=[C:6]2[CH:7]=[CH:8][C:9]3=[N:10][NH:11][C:12]4[C:13](=[CH:14][N:15]([CH3:36])[CH2:16][C:17]=4[C:18]4[CH2:19][CH2:20][N:21]([CH:24]5[CH2:29][CH2:28][C:27](=[C:30]([CH3:35])[C:31]([O:33]C)=[O:32])[CH2:26][CH2:25]5)[CH2:22][CH:23]=4)[C:4](=[C:5]23)[CH:3]=1.[Li+].[OH-].Cl>O1CCCC1.CO>[F:1][C:2]1[CH:37]=[C:6]2[CH:7]=[CH:8][C:9]3=[N:10][NH:11][C:12]4[C:13](=[CH:14][N:15]([CH3:36])[CH2:16][C:17]=4[C:18]4[CH2:19][CH2:20][N:21]([CH:24]5[CH2:25][CH2:26][C:27](=[C:30]([CH3:35])[C:31]([OH:33])=[O:32])[CH2:28][CH2:29]5)[CH2:22][CH:23]=4)[C:4](=[C:5]23)[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of Example 174B (110 mg, 0.151 mmol) in a mixture of tetrahydrofuran (1 mL) and methanol (0.5 mL) was added LiOH (1M aqueous solution, 453 μL, 0.453 mmol). This mixture was heated at 65° C. for 5 hours. After cooling, the reaction was neutralized with 1M aqueous hydrochloride acid. The formed solid was collected by filtration, washed with water and hexanes, and dried in vacuo to provide the title compound. 1H NMR (400 MHz, Pyridine-d5) δ 1.51-2.22 (m, 8H), 2.12 (s, 3H), 2.74 (d, J=13.3 Hz, 1H), 2.93 (s, 3H), 2.95-3.15 (m, 3H), 3.53-3.79 (m, 3H), 4.38 (s, 2H), 6.11 (d, J=3.4 Hz, 1H), 7.27 (td, J=8.3, 7.6, 4.2 Hz, 2H), 7.44 (d, J=5.3 Hz, 1H), 7.89 (dd, J=10.4, 3.0 Hz, 1H), 8.62 (d, J=5.2 Hz, 1H), 12.78 (s, 1H). MS (ESI+) m/z 487.1 (M+H)+.

Workup

temperatureAfter cooling
filtrationThe formed solid was collected by filtration
washwashed with water and hexanes
customdried in vacuo

Sources & evidence

ORD record: ord-00357b374acc43af92616f902077aa33
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328112B2

Reaction notes

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