Diethyl Ether → (2S)-2-[(tert-Butoxycarbonyl)amino]-3-(2'-methoxy[1,1'-biphenyl]-4-yl)propanoic acid

HRID 1078674Notes

Reaction equation

HRID 1078674 reaction equation
C[O:2][C:3](=[O:28])[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[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:24]([O:23][C:21]([NH:20][C@@H:4]([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:22])([CH3:26])([CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 10126493(S)-2-tert-butoxycarbonylamino-3-(2'-methoxy-biphenyl-4-yl)propionic acid methyl ester

Product 1

HCID 22952063(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(2'-methoxy[1,1'-biphenyl]-4-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (S)-N-t-butoxycarbonylamino-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)-N-t-butoxycarbonylamino-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-38a9278f90734adc8d814f76e562eef7
Source dataset
uspto-grants-1996_08
Patent number
US05550119

Reaction notes

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