Diethyl Ether → HCID 67854689, compound

HRID 327617Notes

Reaction equation

HRID 327617 reaction equation
C[O:2][C:3](=[O:28])[C@:4]([NH2:27])([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[CH:8][CH:7]=1.[OH-].[Na+].CCOCC>O>[C:23]([O:22][C:20]([C@:4]([NH2:27])([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[CH:10][CH:11]=1)[C:3]([OH:28])=[O:2])=[O:21])([CH3:25])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 67854709HCID 67854709, compound

Product 1

HCID 67854689HCID 67854689, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (S)-2-t-butoxycarbonyl-amino-3-(2'-methoxybiphenyl-4-yl)-propionic acid methyl ester (4.1 g in methanolic 1N sodium hydroxide (60 mL) is stirred at room temperature for 3 hours. Ether (30 mL) and water (30 mL) are added. The aqueous layer is separated and acidified with concentrated HCl, then extracted with ether (2×20 mL) and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gives (S)-2-t-butoxycarbonyl-amino-3-(2'-methoxybiphenyl-4-yl)-propionic acid.

Workup

  1. customThe aqueous layer is separated
  2. extractionextracted with ether (2×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9f47ad36ea5a46ad848d8915ea740b19
Source dataset
uspto-grants-1993_12
Patent number
US05273990

Reaction notes

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