Lithium hydroxide, monohydrate → HCID 57979889, compound

HRID 1867734Notes

Reaction equation

HRID 1867734 reaction equation
O.[OH-].[Li+].[CH2:4]([O:11][C:12]([NH:14][C@H:15]([C:21]([O:23]C)=[O:22])[CH2:16][O:17][CH:18]([CH3:20])[CH3:19])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.S([O-])(O)(=O)=O.[K+]>O1CCCC1.O>[CH2:4]([O:11][C:12]([NH:14][C@H:15]([C:21]([OH:23])=[O:22])[CH2:16][O:17][CH:18]([CH3:20])[CH3:19])=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516920Potassium bisulfateHCID 57979844HCID 57979844, compound

Product 1

HCID 57979889HCID 57979889, compound

Reagents, catalysts & solvents 1

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

Procedure

Lithium hydroxide monohydrate (0.078 g, 1.86 mmol) was added to a stirred solution of methyl N-[(benzyloxy)carbonyl]-O-isopropyl-L-serinate (0.432 g, 1.47 mmol) in a mixture of tetrahydrofuran/water (10 ml, 1:1) at 0° C. The reaction mixture was stirred overnight, acidified with a 10% w/v aqueous solution of potassium hydrogensulfate and extracted with EtOAc (2×30 ml). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated to give N-[(benzyloxy)carbonyl]-O-isopropyl-L-serine as a clear colourless oil, (0.346 g, 84%); 1H NMR Spectrum: (CDCl3) 1.14 (m, 6H), 3.64 (m, 2H), 3.95 (m, 1H), 4.49 (m, 1H), 5.14 (s, 2H), 5.62 (d, 1H), 7.36 (m, 5H).

Workup

  1. extractionextracted with EtOAc (2×30 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-196f61d6ac534e04bcf4ddd3ebca5afb
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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