Lithium Hydroxide → HCID 71526608, compound

HRID 1843208Notes

Reaction equation

HRID 1843208 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[CH2:53][CH2:52][N:42]2[C:43]3[CH2:44][C:45]([F:51])([F:50])[CH2:46][CH2:47][C:48]=3[CH:49]=[C:41]2[C:40]1=[O:54])(=O)C.[OH-].[Li+]>C(O)(C)C.C1COCC1.O>[F:51][C:45]1([F:50])[CH2:44][C:43]2[N:42]3[CH2:52][CH2:53][N:39]([C:7]4[CH:8]=[C:9]([F:38])[CH:10]=[C:11]([C:12]5[CH:17]=[C:16]([NH:18][C:19]6[CH:24]=[CH:23][C:22]([N:25]7[CH2:30][CH2:29][N:28]([CH:31]8[CH2:32][O:33][CH2:34]8)[CH2:27][C@@H:26]7[CH3:35])=[CH:21][N:20]=6)[C:15](=[O:36])[N:14]([CH3:37])[CH:13]=5)[C:6]=4[CH2:5][OH:4])[C:40](=[O:54])[C:41]3=[CH:49][C:48]=2[CH2:47][CH2:46]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86683737HCID 86683737, compound

Product 1

HCID 71526608HCID 71526608, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 113q (37 mg, 0.05 mmol) and lithium hydroxide (12 mg, 0.5 mmol) in i-propanol/THF (1:1, 4 mL) and water (1 mL) was stirred at 30° C. for 1 h. The mixture was evaporated under reduced pressure. Water (10 mL) was added to the residue and the resulting mixture was extracted with ethyl acetate (2×10 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 113 (20 mg, 57%) as a white solid. MS: [M+H]+ 704.3. 1H NMR (500 MHz, CDCl3) δ 8.57-8.54 (m, 1H), 7.95 (d, J=3.0 Hz, 1H), 7.82 (d, J=3.5 Hz, 1H), 7.45-7.41 (m, 1H), 7.32 (d, J=8.5 Hz, 1H), 7.19-7.16 (m, 1H), 6.99-6.95 (m, 1H), 6.88 (d, J=6.5 Hz, 1H), 6.82 (d, J=8.5 Hz, 1H), 5.97 (d, J=11.5 Hz, 1H), 4.71-4.64 (m, 4H), 4.54 (d, J=12.0 Hz, 1H), 4.35-4.18 (m, 5H), 3.99-3.95 (m, 1H), 3.71 (s, 3H), 3.53 (t, J=6.0 Hz, 1H), 3.47-3.45 (m, 1H), 3.17 (t, J=12.0 Hz, 1H), 3.08 (t, J=5.0 Hz, 2H), 2.90 (t, J=8.5 Hz, 1H), 2.79 (t, J=6.0 Hz, 1H), 2.66-2.63 (m, 1H), 2.56 (d, J=11.0 Hz, 1H), 2.49-2.47 (m, 2H), 2.30-2.20 (m, 2H), 0.99 (d, J=6.0 Hz, 3H).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionWater (10 mL) was added to the residue
  3. extractionthe resulting mixture was extracted with ethyl acetate (2×10 mL)
  4. concentrationThe combined organic layer was concentrated under reduced pressure
  5. customthe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-2b9690b4abde43fbb87eebaab192d2de
Source dataset
uspto-grants-2015_02
Patent number
US08946213B2

Reaction notes

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