Isopropanol → HCID 71525352, compound

HRID 1843250Notes

Reaction equation

HRID 1843250 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([C:12]2[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][N:28]([CH:31]5[CH2:34][O:33][CH2:32]5)[CH2:27][C@H:26]4[CH3:35])=[CH:21][N:20]=3)[C:15](=[O:36])[N:14]([CH3:37])[CH:13]=2)=[CH:10][C:9]([F:38])=[CH:8][C:7]=1[N:39]1[CH2:50][CH2:49][N:48]2[C:41](=[CH:42][C:43]3[CH2:44][C:45]([CH3:52])([CH3:51])[CH2:46][C:47]=32)[C:40]1=[O:53])(=O)C.[OH-].[Li+].C1COCC1.C(O)(C)C>O>[F:38][C:9]1[CH:10]=[C:11]([C:12]2[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][N:28]([CH:31]5[CH2:34][O:33][CH2:32]5)[CH2:27][C@H:26]4[CH3:35])=[CH:21][N:20]=3)[C:15](=[O:36])[N:14]([CH3:37])[CH:13]=2)[C:6]([CH2:5][OH:4])=[C:7]([N:39]2[CH2:50][CH2:49][N:48]3[C:47]4[CH2:46][C:45]([CH3:52])([CH3:51])[CH2:44][C:43]=4[CH:42]=[C:41]3[C:40]2=[O:53])[CH:8]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86683760HCID 86683760, compound

Product 1

HCID 71525352HCID 71525352, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 124a (59 mg, 0.080 mmol), lithium hydroxide (19 mg, 0.80 mmol), THF (10 mL), i-propanol (8 mL), and water (10 mL) was stirred at room temperature for 1.5 h. It was then concentrated under reduced pressure and the residue was extracted with dichloromethane (2×10 mL). The combined dichloromethane extract was concentrated under reduced pressure. The residue was purified with reverse-phase prep-HPLC to afford 124 (43 mg, 79%). MS: [M+H]+ 682.3. 1H NMR (500 MHz, DMSO-d6) δ 8.58-8.57 (m, 1H), 8.41 (s, 1H), 7.84 (d, J=3.0 Hz, 1H), 7.37-7.31 (m, 3H), 7.22 (d, J=9.5 Hz, 1H), 7.19-7.16 (m, 1H), 6.50 (s, 1H), 4.87 (d, J=2.0 Hz, 1H), 4.57-4.53 (m, 2H), 4.46 (t, J=6.0 Hz, 1H), 4.41 (t, J=6.0 Hz, 1H), 4.31 (d, J=3.0 Hz, 2H), 4.21-4.18 (m, 2H), 4.15-4.10 (m, 1H), 3.88-3.85 (m, 1H), 3.67 (d, J=2.0 Hz, 1H), 3.58 (s, 3H), 3.41-3.37 (m, 2H), 3.10-3.07 (m, 1H), 2.95-2.91 (m, 1H), 2.56 (d, J=1.5 Hz, 2H), 2.41 (s, 2H), 2.32-2.28 (m, 2H), 2.17-2.15 (m, 1H), 1.21 (s, 6H), 0.91 (d, J=6.5 Hz, 3H)

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. extractionthe residue was extracted with dichloromethane (2×10 mL)
  3. extractionThe combined dichloromethane extract
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified with reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-4c2a5617a3e24ebea33ca9f4348e5638
Source dataset
uspto-grants-2015_02
Patent number
US08946213B2

Reaction notes

Loading…