Hydrochloric Acid → HCID 66879582, compound

HRID 269597Notes

Reaction equation

HRID 269597 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:12]=1[CH2:13][C:14]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(C(OCC)=O)[C:15]([O:17]CC)=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)C.Cl>O>[CH2:3]([O:10][C:11]1[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:12]=1[CH2:13][CH:14]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:15]([OH:17])=[O:16])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 66879924Diethyl 2-(2-benzyloxy-5-iodobenzyl)-2-tert-butoxycarbonylaminomalonate

Product 1

HCID 66879582HCID 66879582, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

400 ml of a 1N sodium hydroxide solution are added to a suspension of 58 g (97 mmol) of diethyl 2-(2-benzyloxy-5-iodobenzyl)-2-tert-butoxycarbonylaminomalonate (Example 5A) in 800 ml of a mixture of ethanol and water (7:3). After 3 h under reflux and after cooling to room temperature, the pH of the reaction mixture is adjusted to about pH 2 with conc. hydrochloric acid. The reaction mixture is evaporated. 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. After drying in vacuo 47 g (97% of theory) of product are obtained.

Workup

  1. temperatureAfter 3 h under reflux
  2. customThe reaction mixture is evaporated
  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. customAfter drying in vacuo 47 g (97% of theory) of product
  8. customare obtained

Sources & evidence

ORD record
ord-bf03baa7d5374c4e832a638e0886642c
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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