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Methyl bromoacetate → HCID 11012923, compound

HRID 1374417
Notes
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Reaction equation

HRID 1374417 reaction equation
[NH2:1][C@H:2]([CH3:12])[CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].[CH:19](N(C(C)C)CC)([CH3:21])[CH3:20].Cl[C:29]([O-:31])=[O:30]>CO.O>[CH2:20]([O:31][C:29]([N:1]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C@H:2]([CH3:12])[CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[O:30])[CH:19]=[CH2:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 60984Methyl bromoacetate2×HCID 81531Diisopropylethylamine3×HCID 21226386CarbonochloridateHCID 58781983HCID 58781983, compound

Product 1

HCID 11012923HCID 11012923, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tert-butyl(4R)-4-aminopentanoate (2.1 g) prepared above, methyl bromoacetate (1.6 ml, 16.9 mmol) and diisopropylethylamine (3.0 ml, 17.2 mmol) in methanol (60 ml) was stirred at 60° C. for 1 hour. Additional methyl bromoacetate (0.3 ml, 3.2 mmol) and diisopropylethylamine (0.6 ml, 3.4 mmol) were added thereto and the mixture was stirred for 1 hour. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in chloroform (40 ml). To the solution was added ally chloroformate (2.4 ml, 22.6 mmol) and then diisopropylethylamine (4.0 ml, 23.0 mmol). The mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added water and the mixture was extracted three times with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified with silica gel chromatography to give tert-butyl(4R)-4-[[(allyloxy)carbonyl](2-methoxy-2-oxoethyl)amino]pentanoate (3.1 g).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in chloroform (40 ml)
  5. stirringThe mixture was stirred at the same temperature for 1 hour
  6. extractionthe mixture was extracted three times with chloroform
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-3b34bfbbcd7b4e398d52c960945f7c5d
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07163936B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes