Lithium Hydroxide → HCID 69893790, compound

HRID 2121250Notes

Reaction equation

HRID 2121250 reaction equation
C[O:2][C:3](=[O:54])[C@H:4]([CH2:6][C:7]([C:10](=[O:53])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:18][C:19]2[N:20]=[CH:21][N:22]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=2)[C:12]=1[C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][CH:44]=1)([CH3:9])[CH3:8])[NH2:5].[Li+].[OH-]>C1COCC1.O>[C:24]([N:22]1[CH:23]=[C:19]([CH2:18][NH:17][C:13]2[C:12]([C:43]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[CH:46]=[CH:45][CH:44]=3)=[C:11]([CH:16]=[CH:15][CH:14]=2)[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C@@H:4]([C:3]([OH:54])=[O:2])[NH2:5])=[O:53])[N:20]=[CH:21]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69892962HCID 69892962, compound

Product 1

HCID 69893790HCID 69893790, compound

Reagents, catalysts & solvents 1

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

Procedure

The compound of Example 388A (0.24 g, 0.34 mmoles) was dissolved in 10 mL of THF/H2O (2:1) and LiOH (0.029 g, 0.68 mmoles) was added. The reaction was stirred at room temperature for 2 h. The THF was evaporated and the residue dissolved in 15 mL water, and 1N HCl added to lower the pH to 2. The compound is then extracted with ethyl acetate (3×25 mL), dried and the solvents evaporated to afford the free carboxylic acid as a white solid. (0.20 g, 84%).

Workup

  1. customThe THF was evaporated
  2. dissolutionthe residue dissolved in 15 mL water
  3. addition1N HCl added
  4. extractionThe compound is then extracted with ethyl acetate (3×25 mL)
  5. customdried
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-58ba8f725afb4f55a918bf1c67e166db
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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