Methanol → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-methoxypyridin-4-yl)propanoic acid

HRID 339954Notes

Reaction equation

HRID 339954 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Li+].O1CCOCC1.Cl>O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 86681449Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-methoxypyridin-4-yl)propanoate

Product 1

HCID 86681448(2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-methoxypyridin-4-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-methoxypyridin-4-yl)propanoate (1.42 g, 4.58 mmol) was mixed with methanol (10.0 mL) and a solution of lithium hydroxide (0.66 g, 14 mmol) in water (5.0 mL). The mixture was stirred at rt for 1 h. The mixture was then acidified with 4 N HCl dioxane solution and condensed under vacuum directly to give the white solid mixture, which was used directly in the next step. LC-MS found: 297.1 (M+H)+.

Workup

  1. customto give the white solid mixture, which

Sources & evidence

ORD record
ord-978dd80c7cf44bd48c3bbd52e5d74859
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…