Lithium hydroxide, monohydrate → HCID 67077070, compound

HRID 1348629Notes

Reaction equation

HRID 1348629 reaction equation
C([O:3][C:4](=[O:26])[CH:5]([N:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]([CH:8]1[CH2:10][CH2:9]1)[OH:7])C.O.[OH-].[Li+]>O1CCCC1.O>[CH:8]1([CH:6]([OH:7])[CH:5]([N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]([OH:26])=[O:3])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67076976HCID 67076976, compound

Product 1

HCID 67077070HCID 67077070, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 17.1 g (48.5 mmol) racemic (2R,3S and 2S,3R)-3-cyclopropyl-2-dibenzylamino-3-hydroxy-propionic acid ethyl ester in 446 ml tetrahydrofurane were added 8.22 g (194 mmol) lithium hydroxide monohydrate dissolved in 74 ml water. The mixture was stirred at 60° C. overnight. The organic solvent was removed by distillation. Sodium dihydrogenphosphate was added followed by extraction with ethyl acetate. Chromatography on silicagel with diethylether/heptane (1:1 to 1:0) yielded 9.03 g (57%) racemic (2R,3S and 2S,3R)-3-cyclopropyl-2-dibenzylamino-3-hydroxy-propionic acid, MS m/e (%): 326.1 (M+H+, 100).

Workup

  1. customThe organic solvent was removed by distillation
  2. additionSodium dihydrogenphosphate was added
  3. extractionfollowed by extraction with ethyl acetate

Sources & evidence

ORD record
ord-0b817ab1150b46daa1ab2afbc1ae0511
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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