Lithium Hydroxide → N-[(5-tert-butoxycarbonylthiophen-2-yl)methyl]-N-methyl-L-leucine lithium salt

HRID 529216Notes

Reaction equation

HRID 529216 reaction equation
C[O:2][C:3](=[O:24])[C@H:4]([CH2:20][CH:21]([CH3:23])[CH3:22])[N:5]([CH2:7][C:8]1[S:9][C:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:12]=1)[CH3:6].[OH-].[Li+:26]>CO.O1CCCC1>[Li+:26].[C:16]([O:15][C:13]([C:10]1[S:9][C:8]([CH2:7][N:5]([CH3:6])[C@H:4]([C:3]([O-:24])=[O:2])[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:12][CH:11]=1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 90107000N-[(5-tert-butoxycarbonylthiophen-2-yl)methyl]-N-methyl-L-leucine methyl ester

Product 1

HCID 90107093N-[(5-tert-butoxycarbonylthiophen-2-yl)methyl]-N-methyl-L-leucine lithium salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (0.87 g, 2.4 mmol) obtained in step 1 was dissolved in methanol (2.7 mL) and tetrahydrofuran (5.4 mL), 1N aqueous lithium hydroxide solution (2.7 mL) was added, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was lyophilized to give the title compound (0.83 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added

Sources & evidence

ORD record
ord-10db9cde73e744afab8004bee3ca1c64
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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