Lithium Hydroxide → HCID 71526523, compound

HRID 1843166Notes

Reaction equation

C([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[CH:32]=[C:31]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([N:40]3[CH2:45][CH2:44][N:43]([CH3:46])[C@@H:42]([CH3:47])[CH2:41]3)=[CH:36][N:35]=2)[C:30](=[O:48])[N:29]([CH3:49])[CH:28]=1)(=O)C.[OH-].[Li+]>>[CH3:47][C@@H:42]1[N:43]([CH3:46])[CH2:44][CH2:45][N:40]([C:37]2[CH:38]=[CH:39][C:34]([NH:33][C:31]3[C:30](=[O:48])[N:29]([CH3:49])[CH:28]=[C:27]([C:7]4[C:6]([CH2:5][OH:4])=[C:11]([N:12]5[CH2:24][CH2:23][N:15]6[C:16]7[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=7[CH:22]=[C:14]6[C:13]5=[O:25])[CH:10]=[C:9]([F:26])[CH:8]=4)[CH:32]=3)=[N:35][CH:36]=2)[CH2:41]1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 86683710HCID 86683710, compound

Product 1

HCID 71526523HCID 71526523, compoundYield 36%

Procedure

Following the procedures in Example 108, hydrolysis of 107f (60 mg) with lithium hydroxide gave 107 as a white solid (20 mg, 36%). LCMS: [M+H]+ 626. 1H NMR (500 MHz, CDCl3) δ: 8.55 (s, 1H), 7.90 (d, J=2.5, 1H), 7.77 (s, 1H), 7.46 (d, J=2.5, 1H), 7.26 (dd, J=3.0, 9.5, 1H), 7.17 (dd, J=3.0, 9.5, 1H), 6.95 (dd, J=3.0, 9.0, 1H), 6.87 (s, 1H), 6.81 (d, J=9.0, 1H), 4.55 (d, J=10.5, 1H), 4.31-4.36 (m, 2H), 4.14-4.20 (m, 3H), 3.90-3.92 (m, 1H), 3.70 (s, 3H), 3.38 (d, J=11, 1H), 3.32 (d, J=11.5, 1H), 2.94 (s, 2H), 2.56-2.61 (m, 5H), 2.49 (s, 1H), 2.38 (s, 4H), 1.89-1.91 (m, 2H), 1.79-1.80 (m, 2H), 1.17 (d, J=5.0, 3H)

Sources & evidence

ORD record: ord-ed94af57a560406d99359282ab578dd5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946213B2

Reaction notes

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