Sodium Chloride → HCID 86693760, compound

HRID 2279252Notes

Reaction equation

HRID 2279252 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([CH2:19]C(O)=O)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC([O:27][CH2:28]C)=O.[N-:30]=[N+]=[N-].[Na+].[Na+].[Cl-]>C1COCC1.O>[O:27]=[C:28]1[NH:30][CH2:19][C@H:10]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:23])[N:11]1[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 11759109Boc-D-Asp-OBzl

Product 1

HCID 86693760HCID 86693760, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of Boc-D-Aspartic acid-1-benzyl ester (0.250 g, 0.77 mmol) taken in THF (4 mL), cooled to −10° C., Ethyl chloroformate (0.11 ml, 1.1 mmol) and TEA (0.34 ml, (2.47 mmol) was added and stirred for 30 min. NaN3 (0.25 g, 0.386 mmol) was dissolved in water (4 ml) and added portion wise to the reaction mixture maintaining the temperature at −10° C. The reaction mixture was slowly warmed to room temperature and stirred for further 2 h. After completion of reaction (by TLC), the reaction mixture was poured into saturated NaCl solution and extracted with EtOAc (2×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to half of the volume; PhMe (15 mL) was added and heated to 80° C. for 4 h. After completion (by TLC), the reaction mixture was poured into saturated NaCl solution and extracted with EtOAc (2×15 mL). The combined organic extracts were dried over Na2SO4 and purified by column chromatography to afford 25a (0.11 g, 44%) as a brown sold.

Workup

  1. additionadded portion wise to the reaction mixture
  2. temperaturemaintaining the temperature at −10° C
  3. temperatureThe reaction mixture was slowly warmed to room temperature
  4. stirringstirred for further 2 h
  5. customAfter completion of reaction (by TLC)
  6. extractionextracted with EtOAc (2×10 mL)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated under reduced pressure to half of the volume
  9. additionPhMe (15 mL) was added
  10. temperatureheated to 80° C. for 4 h
  11. additionAfter completion (by TLC), the reaction mixture was poured into saturated NaCl solution
  12. extractionextracted with EtOAc (2×15 mL)
  13. dry with materialThe combined organic extracts were dried over Na2SO4
  14. custompurified by column chromatography

Sources & evidence

ORD record
ord-6cf68ebf6bfa4e64a5009f27471ae867
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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