Lithium Hydroxide → HCID 68879396, compound

HRID 724551Notes

Reaction equation

HRID 724551 reaction equation
C[CH:2]([CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][C@@H:25]2[OH:28])[C@:21]2([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]4[CH:39]=[CH:38][C:37]([C@H:40]5[CH2:57][C@@:55]6([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]6([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]6[C:41]5=[C:42]5[C:47]([CH2:48][CH2:49]6)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]5)=[CH:36][C:35]=4[F:63])[CH3:33])[CH2:19][CH2:20]2)[CH2:15][C@H:14]3[OH:64])[CH2:11][CH2:10]1)[CH3:8])[C:3]([OH:5])=[O:4].[Li+].[OH-]>C1COCC1.CO>[OH:64][C@@H:14]1[CH2:15][C@H:16]2[C@:21]([CH3:22])([CH2:20][CH2:19][C@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]3[CH:39]=[CH:38][C:37]([C@H:40]4[CH2:57][C@@:55]5([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]5([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]5[C:41]4=[C:42]4[C:47]([CH2:48][CH2:49]5)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]4)=[CH:36][C:35]=3[F:63])[CH3:33])[CH2:17]2)[C@@H:23]2[C@@H:13]1[C@H:12]1[C@:26]([CH3:27])([C@@H:25]([OH:28])[CH2:24]2)[C@@H:9]([C@H:7]([CH3:8])[CH2:6][CH2:2][C:3]([OH:5])=[O:4])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 131726115HCID 131726115, compound

Product 1

HCID 68879396HCID 68879396, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 3D (360 mg, 0.408 mmol) was dissolved in 6 ml of THF and CH3OH (1:1). Then 2.5 ml of LiOH solution (1M, aqueous) was added at 0° C. The resulting mixture was stirred for 5 hour at ambient temperature. The organic solvent was removed in vacuo, and enough water was added to make one phase. The solution was acidified with acetic acid to precipitate a light yellow solid, which was extracted with EtOAc (3 times). The combined organic layer was washed with brine and dried over Na2SO4 Concentration in vacuo gave the title compound (350 mg, 98% yield). 1H NMR (300 MHz, CDCl3) δ 6.83–6.74 (m, 3 H), 5.78 (s, 1 H), 4.34 (d, J=7.2 Hz, 1 H), 3.98 (m, 1 H), 3.84 (m, 1 H), 3.52–3.33 (m, 5H), 2.92 (s, 3H), 2.80–1.10 (m, 44H), 1.89 (s, 3H), 0.99 (d, J=6.0 Hz, 3 H), 0.89 (s, 3 H), 0.69 (s, 3 H), 0.55 (s, 3 H); MS (ESI) m/e 868 (M+H)+, 866 (M−H)—.

Workup

  1. customThe organic solvent was removed in vacuo, and enough water
  2. additionwas added
  3. customto precipitate a light yellow solid, which
  4. extractionwas extracted with EtOAc (3 times)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4 Concentration in vacuo

Sources & evidence

ORD record
ord-1914282855324045ad5eee0ee02fdb92
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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