Lithium hydroxide, monohydrate → HCID 53248162, compound

HRID 1914448Notes

Reaction equation

HRID 1914448 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([S:17]([OH:20])(=[O:19])=[O:18])[CH2:11][C:12]([O:14]CC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([S:17]([OH:20])(=[O:18])=[O:19])[CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53248161HCID 53248161, compound

Product 1

HCID 53248162HCID 53248162, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

1-(tert-Butoxycarbonylamino)-4-ethoxy-4-oxobutane-2-sulfonic acid (402 mg, 1.29 mmol) in the mixture of THF/H2O (1:2, 60 ml) was added lithium hydroxide monohydrate (2.0 g, 47.6 mmol). The mixture was stirred under Ar overnight, concentrated, purified on C-18 column (2×30 cm) eluted with from 100% water to 10% methanol in water to afford 328 mg (90%) of the title compound. 1H NMR (DMSO), 6.78 (s, 1H), 4.03 (m, 1H), 3.57 (dd, 1H, J=4.2, 13.4 Hz), 3.41 (m, 1H), 2.89 (m, 1H), 2.61 (m, 1H), 1.39 (s, 9H); 13C NMR 174.21, 155.82, 79.85, 59.95, 42.06, 32.52, 28.88, 14.55; ESI MS 281.8 (M−H);

Workup

  1. concentrationconcentrated
  2. custompurified on C-18 column (2×30 cm)
  3. washeluted with from 100% water to 10% methanol in water

Sources & evidence

ORD record
ord-20f6b0ada66348e8bc0b5faec40dcff0
Source dataset
uspto-grants-2013_12
Patent number
US08613930B2

Reaction notes

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