Lithium Hydroxide → 2-Amino-2-[2-(4'-hexylbiphenyl-4-yl)-ethyl]propane-1,3-diol

HRID 1375921Notes

Reaction equation

HRID 1375921 reaction equation
C([O:4][CH2:5][C:6]([NH:32]C(=O)C)([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:7][O:8]C(=O)C)(=O)C.[Li+].[OH-]>C1COCC1.O>[NH2:32][C:6]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)([CH2:7][OH:8])[CH2:5][OH:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69429205HCID 69429205, compound

Product 1

HCID 114169572-Amino-2-[2-(4'-hexylbiphenyl-4-yl)-ethyl]propane-1,3-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid 2-acetoxymethyl-2-acetylamino-4-(4′-hexyl-biphenyl-4-yl)-butyl ester (0.2 mmol) is dissolved in THF (1 mL) and treated with 2 N LiOH aqueous solution (0.5 mL). The resulting mixture is stirred at reflux for 1 h and diluted with H2O (10 mL). It is then extracted with EtOAc (3×5 mL) and the combined organic phase is washed with brine and dried over Na2SO4. After concentrating, the crude product is purified with LC-MS to give the desired product as a white solid. MS: (ES+): 356.2 (M+1)+.

Workup

  1. temperatureat reflux for 1 h
  2. extractionIt is then extracted with EtOAc (3×5 mL)
  3. washthe combined organic phase is washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrating
  6. customthe crude product is purified with LC-MS

Sources & evidence

ORD record
ord-7ec367089ffd43188821aad894c5552a
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

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