Lithium Hydroxide → HCID 58380396, compound

HRID 404402Notes

Reaction equation

HRID 404402 reaction equation
[F:1][C:2]1[C:3]([C:10]2[CH:33]=[CH:32][C:13]([CH2:14][O:15][C:16]3[CH:24]=[C:23]4[C:19]([CH2:20][CH2:21][C@@:22]54[CH2:26][C@H:25]5[C:27]([O:29]CC)=[O:28])=[CH:18][CH:17]=3)=[CH:12][C:11]=2[C:34]([CH3:38])([CH:36]=[CH2:37])[CH3:35])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[OH-].[Li+]>CO>[F:1][C:2]1[C:3]([C:10]2[CH:33]=[CH:32][C:13]([CH2:14][O:15][C:16]3[CH:24]=[C:23]4[C:19]([CH2:20][CH2:21][C@@:22]54[CH2:26][C@H:25]5[C:27]([OH:29])=[O:28])=[CH:18][CH:17]=3)=[CH:12][C:11]=2[C:34]([CH3:38])([CH:36]=[CH2:37])[CH3:35])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58379771HCID 58379771, compound

Product 1

HCID 58380396HCID 58380396, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction mixture of compound 123.1 (48.4 mg, 94 μmol) and lithium hydroxide (0.25 mL 3.3 M LiOH(aq), 0.75 mmol) in MeOH (0.6 m 1) was stirred at room temperature for 3 hours. The resulting mixture was purified by preparative HPLC (reverse phase) to give Example 123 (30.0 mg, 66% yield over two steps). MS ESI (pos.) M/E: 488.2 (M+H). 1H-NMR (500 MHz, CDCl3) δ ppm 7.94 (1H, s), 7.58 (1H, s), 7.33 (1H, d, J=7.8 Hz), 7.15 (1H, d, J=8.1 Hz), 7.00 (1H, d, J=7.8 Hz), 6.85 (1H, dd, J=8.3, 2.4 Hz), 6.62 (1H, d, J=4.9 Hz), 6.36 (1H, d, J=2.2 Hz), 5.96 (1H, dd, J=17.5, 10.6 Hz), 5.05 (2H, s), 4.71-4.86 (2H, m), 3.88 (3H, s), 2.93-3.05 (2H, m), 2.39 (1H, dd, J=8.3, 6.2 Hz), 2.32 (1H, dd, J=8.3, 6.2 Hz), 1.96-2.06 (1H, m), 1.70 (1H, t, J=5.4 Hz), 1.51 (1H, dd, J=8.3, 4.8 Hz), 1.27 (3H, s), 1.25 (3H, s).

Workup

  1. customThe resulting mixture was purified by preparative HPLC (reverse phase)
  2. customto give Example 123 (30.0 mg, 66% yield over two steps)

Sources & evidence

ORD record
ord-e2fcfe3424dd4517b150c88f7cc9410e
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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