Lithium Hydroxide → HCID 67973799, compound

HRID 880612Notes

Reaction equation

HRID 880612 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH:8]=[CH:9][N:10]([C:15]3[CH:16]=[N:17][CH:18]=[C:19]([C@@H:21]4[CH2:25][CH2:24][CH2:23][N:22]4[C:26](=[O:45])[C@@H:27]([NH:31][C:32](=[O:44])[C@@H:33]([N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH3:36])[CH3:34])[CH:28]([CH3:30])[CH3:29])[CH:20]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[C:40]([O:39][C:37]([N:35]([CH3:36])[C@@H:33]([CH3:34])[C:32]([NH:31][C@@H:27]([CH:28]([CH3:29])[CH3:30])[C:26]([N:22]1[CH2:23][CH2:24][CH2:25][C@H:21]1[C:19]1[CH:20]=[C:15]([N:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:6]([C:4]([OH:5])=[O:3])[C:7]=3[CH:8]=[CH:9]2)[CH:16]=[N:17][CH:18]=1)=[O:45])=[O:44])=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 67973772HCID 67973772, compound

Product 1

HCID 67973799HCID 67973799, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[5-((S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-pyrrolidin-2-yl)-pyridin-3-yl]-1H-indole-4-carboxylic acid ethyl ester (I-1A-1d: 1.2 g, 1.9 mmol) in THF (5 mL) and MeOH (1.7 mL) was added a solution of LiOH (0.080 g, 3.5 mmol) in water (1.7 mL). The mixture was stirred at room temperature for 5 hours. More LiOH (0.023 g, 0.97 mmol) was added and stirring continued for overnight. The reaction mixture was quenched with water and concentrated under reduced pressure to remove THF. The remaining mixture was diluted with water and neutralized with 1 M HCl dropwise until pH=4. The white precipitate formed was filtered and dried in vacuo to give the titled compound as a white powder (1.0 g, 87%).

Workup

  1. stirringstirring
  2. waitcontinued for overnight
  3. customThe reaction mixture was quenched with water
  4. concentrationconcentrated under reduced pressure
  5. customto remove THF
  6. additionThe remaining mixture was diluted with water and neutralized with 1 M HCl dropwise until pH=4
  7. customThe white precipitate formed
  8. filtrationwas filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-06014c7306ec4784a1b18999e9f9691a
Source dataset
uspto-grants-2015_03
Patent number
US08993523B2

Reaction notes

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