Lithium hydroxide, monohydrate → 2-(2-((Tert-butoxycarbonylamino)methyl)thiazole-4-carboxamido)-2-methylpropanoic acid

HRID 405689Notes

Reaction equation

HRID 405689 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21]C)=[O:20])=[O:16])[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]([CH3:24])([CH3:23])[C:19]([OH:21])=[O:20])=[O:16])[N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67991992Methyl 2-(2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxamido)-2-methylpropanoate

Product 1

HCID 679919852-(2-((Tert-butoxycarbonylamino)methyl)thiazole-4-carboxamido)-2-methylpropanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(2-((tert-butoxycarbonylamino)methyl) thiazole-4-carboxamido)-2-methylpropanoate (2.4 g, 6.7 mmole) was dissolved in 10 mL methanol and 3 mL water. To the mixture, lithium hydroxide monohydrate (0.56 g, 13.4 mmole) was then added. The reaction was stirred at room temperature until TLC indicated complete consumption of starting material. To the mixture, water and EtOAc were added, and the aqueous layer was acidified with 2 N HCl to about PH 7. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4 and concentrated to provide the desired product as a white solid (2.3 g, quantitative yield).

Workup

  1. customconsumption of starting material
  2. additionTo the mixture, water and EtOAc were added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7b0e8896965e4ce289e81d1659d252ee
Source dataset
uspto-grants-2014_06
Patent number
US08754050B2

Reaction notes

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