Lithium hydroxide, monohydrate → HCID 67077019, compound

HRID 1348660Notes

Reaction equation

HRID 1348660 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([N:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]([OH:9])[CH2:7][CH3:8])C.O.[OH-].[Li+]>O1CCCC1.O>[CH2:18]([N:10]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:5]([CH:6]([OH:9])[CH2:7][CH3:8])[C:4]([OH:25])=[O:3])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67076904HCID 67076904, compound

Product 1

HCID 67077019HCID 67077019, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 17.7 g (51.9 mmol) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-pentanoic acid ethyl ester in 245 ml tetrahydrofurane were added 8.80 g (208 mmol) lithium hydroxide monohydrate dissolved in 44 ml water. The mixture was stirred at 60° C. for 2.5 days and the organic solvent was removed by distillation. Water was added followed by extraction with diethylether. The waterphase was adjusted to pH 1. Extraction with ethylacetate yielded 14.8 g (91%) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-pentanoic acid, MS m/e (%): 314.1 (M+H+, 100).

Workup

  1. customthe organic solvent was removed by distillation
  2. additionWater was added
  3. extractionfollowed by extraction with diethylether
  4. extractionExtraction with ethylacetate

Sources & evidence

ORD record
ord-74ad7085892a475aae55576552602e22
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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