Poly-gamma-benzyl L-glutamate → HCID 21197492, compound

HRID 2369219Notes

Reaction equation

HRID 2369219 reaction equation
N[CH:2]([CH2:6][CH2:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:3]([OH:5])=[O:4].[Br-:18].[K+].C(OC(CCC=O)C(O)=O)C1C=CC=CC=1>Br>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][CH2:6][CH:2]([Br:18])[C:3]([OH:5])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 95441Poly-gamma-benzyl L-glutamateHCID 253877Potassium BromideHCID 17998586HCID 17998586, compound

Product 1

HCID 21197492HCID 21197492, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-5-(benzyloxy)-5-oxopentanoic acid, 20.00 g (0.084 mole), and potassium bromide, 34.1 g (0.29 mole), were dissolved in 80 mL of ˜6N aqueous HBr, previously chilled to 0° C. A stream of nitrogen was bubbled through the solution and the mixture was chilled to −10° C. by means of a cold bath. Sodium nitrite, 6.98 g (0.10 mole) was added in portions over 30 min with stirring, while maintaining the temperature of the reaction from −13° C. to −10° C. After 6 hours stirring at −10° C., the mixture was extracted with ethyl ether, 4×100 mL and the resulting solution dried with magnesium sulfate. The mixture was filtered to remove the drying agent and evaporated to give an orange oil. The oil was purified by flash chromatography, chloroform-hexanes to give a clear and colorless oil. The yield was 11.5 g, i.e., 45%, based on starting 2-amino-5-{[(benzyl-oxy)-5-oxopentanoic acid. NMR is consistent with structure.

Workup

  1. customA stream of nitrogen was bubbled through the solution
  2. temperaturethe mixture was chilled to −10° C. by means of a cold bath
  3. additionSodium nitrite, 6.98 g (0.10 mole) was added in portions over 30 min
  4. temperaturewhile maintaining
  5. customthe temperature of the reaction from −13° C. to −10° C
  6. stirringAfter 6 hours stirring at −10° C.
  7. extractionthe mixture was extracted with ethyl ether, 4×100 mL
  8. dry with materialthe resulting solution dried with magnesium sulfate
  9. filtrationThe mixture was filtered
  10. customto remove the drying agent
  11. customevaporated
  12. customto give an orange oil
  13. customThe oil was purified by flash chromatography, chloroform-hexanes
  14. customto give a clear and colorless oil

Sources & evidence

ORD record
ord-8017dcc71cd34e558594c993949f3916
Source dataset
uspto-grants-2014_04
Patent number
US08703937B2

Reaction notes

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