Hydrochloric Acid → 3-((tert-Butoxycarbonyl)amino)-2-(4-(((triisopropylsilyl)oxy)methyl)phenyl)propanoic acid

HRID 1020110Notes

Reaction equation

HRID 1020110 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[CH:18][CH:17]=1)[C:11]([O:13]CC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:16]1[CH:17]=[CH:18][C:19]([CH2:22][O:23][Si:24]([CH:25]([CH3:27])[CH3:26])([CH:28]([CH3:30])[CH3:29])[CH:31]([CH3:32])[CH3:33])=[CH:20][CH:21]=1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59563809Ethyl 3-((tert-butoxycarbonyl)amino)-2-(4-(((triisopropylsilyl)oxy)methyl)phenyl)propanoate

Product 1

HCID 595637683-((tert-Butoxycarbonyl)amino)-2-(4-(((triisopropylsilyl)oxy)methyl)phenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(tert-butoxycarbonylamino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoate (E202) in methanol was added dropwise 4 N NaOH. The mixture was stirred for 2 h, adjusted the pH to 7 with 2 N HCl, and extracted with ethyl acetate. The combined organic layers were washed with 0.5 N HCl and brine, dried (MgSO4), and concentrated in vacuo to afford 3-(tert-butoxycarbonylamino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoic acid (E203) as white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with 0.5 N HCl and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b434c1905434255a5944724ce5b8c7b
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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