Lithium hydroxide, monohydrate → HCID 22125682, compound

HRID 1857988Notes

Reaction equation

HRID 1857988 reaction equation
[CH2:1]([NH:8][CH:9]([CH2:15][CH2:16][CH:17]1[O:22][CH2:21][CH2:20][CH2:19][O:18]1)[C:10]([O:12]CC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1CO.O>[CH2:1]([NH:8][CH:9]([CH2:15][CH2:16][CH:17]1[O:18][CH2:19][CH2:20][CH2:21][O:22]1)[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22125679HCID 22125679, compound

Product 1

HCID 22125682HCID 22125682, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 66577907Tetrahydrofuran-methanol waterSolvent

Procedure

A mixture of ethyl 2-benzylamino-4-(1,3-dioxan-2-yl)butyrate (77.5 g, 0.252 mol) and lithium hydroxide monohydrate (15.87 g, 0.378 mol) in tetrahydrofuran-methanol-water (1:3:1; 1 L) was stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo and the aqueous residue was diluted with water (200 mL), washed with diethyl ether (200 mL) and freeze dried. The residue was purified by flash chromatography (silica gel, 20-30% MeOH/CH2Cl2) to give 59.5 g (85%) of the title compound as a white solid. δH (360 MHz, d6 -DMSO/D2O) 1.29 (1H, br d, J=13.4 Hz), 1.54 (2H, m), 1.63 (2H, m), 1.79 (1H, m), 3.05 (1H, t, J=6.0 Hz), 3.64 (2H, m), 3.80 (1H, d, J=13.1 Hz), 3.91-3.94 (3H, m), 4.44 (1H, t, J=5.1 Hz), 7.32-7.39 (5H, m), m/e (ES+) 280 (M+H)+, 204 (M-C6H5 +2H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe aqueous residue was diluted with water (200 mL)
  3. washwashed with diethyl ether (200 mL)
  4. customfreeze dried
  5. customThe residue was purified by flash chromatography (silica gel, 20-30% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-262c7897272648c9823b45891a2afff1
Source dataset
uspto-grants-2000_11
Patent number
US06150391

Reaction notes

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