Lithium Hydroxide → 2-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid

HRID 1751453Notes

Reaction equation

HRID 1751453 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([NH:12][C:13]([O:15][CH3:16])=[O:14])[CH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[Li+].[OH-]>C1COCC1.CO>[CH3:16][O:15][C:13]([NH:12][CH:4]([CH2:5][CH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1)[C:3]([OH:17])=[O:2])=[O:14]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 696725082-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester

Product 1

HCID 696729572-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (0.11 g, 1.1 mmol) in THF (3.3 mL) and MeOH (1.1 mL) at 0° C. (external, ice bath) was added aqueous LiOH (1 M, 0.88 mL, 0.88 mmol). The solution was stirred at room temperature for 18 h and concentrated to provide 2-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid which was used crude in the next step. LCMS-ESI+: calc'd for C10H17NO5: 231.11 (M+); Found: 231.99 (M+H+).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-28c6f58d400d4ef48d2a97d0807b0662
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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