Lithium hydroxide, monohydrate → HCID 67076852, compound

HRID 1348667Notes

Reaction equation

HRID 1348667 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([N:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:6]([OH:17])[CH2:7][CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.O.[OH-].[Li+].P([O-])(O)(O)=O.[K+]>O1CCCC1.O>[CH2:10]([O:9][CH2:8][CH2:7][CH:6]([OH:17])[CH:5]([N:18]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:4]([OH:33])=[O:3])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516951Monobasic potassium phosphateHCID 67076827HCID 67076827, compound

Product 1

HCID 67076852HCID 67076852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 13.0 g (29 mmol) racemic (2S,3R and 2R,3S)-5-benzyloxy-2-dibenzylamino-3-hydroxy-pentanoic acid ethyl ester in 150 ml tetrahydrofurane were added 4.88 g (116 mmol) lithium hydroxide monohydrate dissolved in 41 ml water. The mixture was stirred at 60° C. for 16 hours. A 1 M aqueous solution of potassium dihydrogenphosphate was added followed by extraction with ethylacetate. Chromatography on silicagel with heptane/etylacetate 4:1 to 1:1 yielded 8.57 g (70%) racemic (2S,3R and 2R,3S)-5-benzyloxy-2-dibenzylamino-3-hydroxy-pentanoic acid, MS m/e (%): 420.1 (M+H+, 100).

Workup

  1. extractionfollowed by extraction with ethylacetate

Sources & evidence

ORD record
ord-6ee9bf1b99c54e338ef3302c62191767
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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