Hydrochloric Acid → (S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodophenyl)propanoic acid

HRID 1441966Notes

Reaction equation

HRID 1441966 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([I:29])[CH:24]=1)(C(OCC)=O)[C:12]([O:14]CC)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].C(O)C.Cl>O>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:12]([OH:14])=[O:13])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([I:29])[CH:24]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 67189170Diethyl [(tert-butoxycarbonyl)amino](3-iodobenzyl)malonate

Product 1

HCID 11728885(S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

240 ml of a 1N sodium hydroxide solution are added to a suspension of 30.3 g (62 mmol) of diethyl[(tert-butoxycarbonyl)amino](3-iodobenzyl)malonate (Example 7D) in 440 ml of a mixture of ethanol and water (3:1). After 3 h under reflux and after cooling to RT, the pH of the reaction mixture is adjusted with concentrated hydrochloric acid to approx. pH 2. The reaction mixture is concentrated in vacuo. The residue is taken up in MTBE and water. The aqueous phase is extracted three times with MTBE. The combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is purified by RP-HPLC (acetonitrile/water gradient).

Workup

  1. temperatureAfter 3 h under reflux
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. extractionThe aqueous phase is extracted three times with MTBE
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-bd20e7e91c9a4d35ae1231adc7c88dc2
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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