Lithium Hydroxide → HCID 53779144, compound

HRID 2121252Notes

Reaction equation

HRID 2121252 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([CH2:6][CH:7]([CH2:9][C:10](=[O:31])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:12]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:8])[NH2:5].[Li+].[OH-]>C1COCC1.O>[N:22]1[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:13]2[C:12]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:11]([CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][CH:7]([CH3:8])[CH2:6][C@@H:4]([C:3]([OH:32])=[O:2])[NH2:5])=[O:31])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69892307HCID 69892307, compound

Product 1

HCID 53779144HCID 53779144, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

The product of Example 389A (0.22 g, 0.51 mmoles) was dissolved in 10 mL THF/H2O (2:1), cooled to 0° C. and LiOH (0.04 g, 1.02 mmoles) added. The reaction was stirred at 0° C. for 1 h, followed by stirring at room temperature for 2 hours. The solvents were evaporated and the residue passed through a bed of silica gel and eluted with CH2Cl2:CH3OH (9:1) to afford the title compound (0.19 g, 90%) as a white solid. 1H NMR (300 MHz, DMSO-d6) 0.79 (t, 6H), 1.19 (m, 2H), 1.42 (m, 1H), 4.06 (m, 1H), 4.36 (d, 2H), 6.53 (dd, 1H), 6.81 (m, 2H), 7.04 (d, 1H), 7.17-7.31 (m, 6H), 7.59 (d, 1H), 8.46 (d, 2H).

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. customThe solvents were evaporated
  3. washeluted with CH2Cl2:CH3OH (9:1)

Sources & evidence

ORD record
ord-2bbda591179b4ddc8592fff33f1f002f
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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