Lithium Hydroxide → HCID 117777441, compound

HRID 520299Notes

Reaction equation

C([O:4][CH2:5][C:6]1[C:7]([N:21]2[CH2:32][CH2:31][N:30]3[C:23](=[CH:24][C:25]4[CH2:26][C:27]([CH3:34])([CH3:33])[CH2:28][C:29]=43)[C:22]2=[O:35])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH2:18])[C:15](=[O:19])[N:14]([CH3:20])[CH:13]=1)(=O)C.[Li+].[OH-]>CC(O)C.C1COCC1.O>[NH2:18][C:16]1[C:15](=[O:19])[N:14]([CH3:20])[CH:13]=[C:12]([C:11]2[CH:10]=[CH:9][N:8]=[C:7]([N:21]3[CH2:32][CH2:31][N:30]4[C:23](=[CH:24][C:25]5[CH2:26][C:27]([CH3:33])([CH3:34])[CH2:28][C:29]=54)[C:22]3=[O:35])[C:6]=2[CH2:5][OH:4])[CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 103c (1.1 g, 2.3 mmol) and LiOH (450 mg, 11.0 mmol) in iPrOH/THF (1:1, 10 mL) and H2O (2.5 mL) was stirred at 40° C. for 0.5 h. The mixture was evaporated in vacuo. The residue was partitioned between EtOAc and water. The combined EtOAc extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 10:1 dichloromethane/methanol to afford 103d (350 mg, 36%) as a pale yellow solid. MS-ESI: [M+H]+ 434.3. 1H NMR (500 MHz, CDCl3) δ 8.44 (d, J=5.0 Hz, 1H), 7.59 (d, J=2.0 Hz, 1H), 7.21 (d, J=5.0 Hz, 1H), 6.83 (s, 1H), 6.82 (d, J=2.0 Hz, 1H), 5.04-5.03 (m, 1H), 4.63-4.62 (m, 1H), 4.50-4.48 (m, 1H), 4.30-4.28 (m, 1H), 4.16-4.10 (m, 3H), 3.87-3.85 (m, 1H), 3.65 (s, 3H), 2.57-2.56 (m, 2H), 2.50 (s, 2H), 1.26 (s, 6H).

Workup

customThe mixture was evaporated in vacuo
customThe residue was partitioned between EtOAc and water
extractionThe combined EtOAc extract
concentrationwas concentrated under reduced pressure
customthe residue was purified by silica-gel column chromatography
washeluting with 10:1 dichloromethane/methanol

Sources & evidence

ORD record: ord-6a2cff6606ea42e598edb28c5228d522
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326985B2

Reaction notes

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