Lithium Hydroxide → HCID 178514856, compound

HRID 1024081Notes

Reaction equation

HRID 1024081 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[N:35]=[C:34]2[C:30]([N:31]=[CH:32][NH:33]2)=[C:29]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:48][CH2:47][N:46]([CH:49]4[CH2:52][O:51][CH2:50]4)[CH2:45][CH2:44]3)=[CH:39][CH:38]=2)[N:28]=1)(=O)C.[OH-].[Li+]>C(O)(C)C.C1COCC1.O>[F:26][C:9]1[CH:8]=[C:7]([C:27]2[N:35]=[C:34]3[C:30]([N:31]=[CH:32][NH:33]3)=[C:29]([NH:36][C:37]3[CH:42]=[CH:41][C:40]([N:43]4[CH2:44][CH2:45][N:46]([CH:49]5[CH2:50][O:51][CH2:52]5)[CH2:47][CH2:48]4)=[CH:39][CH:38]=3)[N:28]=2)[C:6]([CH2:5][OH:4])=[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]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178475812HCID 178475812, compound

Product 1

HCID 178514856HCID 178514856, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 117h (140 mg, 0.20 mmol) and lithium hydroxide (48 mg, 2.0 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 in vacuo and the residue was diluted with water (5 mL). It was then extracted with ethyl acetate (2×10 mL). The combined ethyl acetate extract was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 117 (85 mg, 64%) as a white solid. MS-ESI: [M+H]+ 664.4. 1H NMR (500 MHz, CDCl3) δ 12.45 (s, 1H), 8.26 (s, 1H), 7.86 (d, J=8.5 Hz, 2H), 7.66 (d, J=8.0 Hz, 2H), 7.11 (d, J=9.0 Hz, 1H), 6.96 (d, J=8.0 Hz, 2H), 6.88 (s, 1H), 4.74-4.68 (m, 4H), 4.66-4.60 (m, 2H), 4.17-4.09 (m, 3H), 3.91-3.90 (m, 1H), 3.59 (t, J=6.5 Hz, 1H), 3.25-3.23 (m, 4H), 2.59-2.52 (m, 8H), 1.89-1.80 (m, 4H).

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionthe residue was diluted with water (5 mL)
  3. extractionIt was then extracted with ethyl acetate (2×10 mL)
  4. extractionThe combined ethyl acetate extract
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-31186ba28d3c473fbf305c6745fe3067
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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