Lithium hydroxide, monohydrate → HCID 118276684, compound

HRID 1053661Notes

Reaction equation

HRID 1053661 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][P:15]([C:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])[CH3:21])([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>O.CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][P:15]([C:20]([O:22][CH2:23][CH3:24])([O:25][CH2:26][CH3:27])[CH3:21])([O:17][CH2:18][CH3:19])=[O:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118276696HCID 118276696, compound

Product 1

HCID 118276684HCID 118276684, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Adapting a literature known protocol (Dayal, et al., Steroids, 1990, 55(5), 233-237), a reaction mixture of methyl(2R)-2-(tert-butoxycarbonylamino)-3-(1,1-diethoxyethyl(ethoxy)-phosphoryl)propanoate (10a) (4.11 g, 10.0 mmol) and commercial lithium hydroxide monohydrate (LiOH.H2O) (839 mg, 20.0 mmol) in a mixture of water (20 mL) and methanol (MeOH) (5 mL) is stirred at room temperature. The reaction is monitored by TLC and/or LC/MS to completion. Acidic aqueous work-up and purification by silica gel column chromatography furnish the title compound (2R)-2-(tert-butoxycarbonylamino)-3-(1,1-diethoxyethyl(ethoxy)phosphoryl)propanoic acid (10b) which may be used directly in the next step without further isolation and purification.

Workup

  1. customAcidic aqueous work-up and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-b78b85ab451a42528d59b6ca900720b0
Source dataset
uspto-grants-2016_07
Patent number
US09394237B2

Reaction notes

Loading…