Lithium Hydroxide → HCID 178460520, compound

HRID 1424197Notes

Reaction equation

HRID 1424197 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:24][C:18]=2[N:17]=1)[CH:10]([CH3:15])[C:11]([O:13]C)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:24][C:18]=2[N:17]=1)[CH:10]([CH3:15])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178500488HCID 178500488, compound

Product 1

HCID 178460520HCID 178460520, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-(5-tert-butyl-1H-benzimidazol-2-yl)-2-methylpropanoate (Preparation 33, 7.25 g, 18.65 mmol) and lithium hydroxide (0.67 g, 27.95 mmol) in THF and water (100 mL/10 mL) was stirred at room temperature for 18 hours. The THF was evaporated and the remaining aqueous solution was diluted with water (100 mL). A solution of KHSO4 in water was added resulting in a white precipitate. The solid was filtered and dried to afford the title compound that was taken directly on to the next step.

Workup

  1. customThe THF was evaporated
  2. additionthe remaining aqueous solution was diluted with water (100 mL)
  3. additionA solution of KHSO4 in water was added
  4. customresulting in a white precipitate
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-4494b3ee88df405296afc03dfed4e833
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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