Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Bromide | HCID 253877 | — |
| Reactant | 5-(Phenylmethyl) hydrogen D-glutamate | HCID 6994624 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Solvent | Sulfuric Acid | HCID 1118 | — |
| Product | HCID 53916216 | HCID 53916216 | 87.3% |
Reaction Steps
To a solution of D-glutamic acid γ-benzyl ester (5.00 g, 21 mmol) and KBr (7.5 g, 63 mmol) in 2.5N H2SO4 (35 mL) at 0° C. (ice bath) was added NaNO2 (2.45 g, 35.5 mmol) in small portions over 1.5 hrs keeping the internal temperature below 5° C. The resulting mixture was stirred at 0° C. for 1 hr and at room temperature for 45 min. The mixture was extracted with Et2O, extract washed with water and saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was taken up in CH2Cl2, re-dried over Na2SO4 and evaporated to dryness to give crude (2R)-2-bromo-4-carbobenzyloxy-butyric acid (5.52 g) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06242422B1 |
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| Source dataset | uspto-grants-2001_06 |
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| ORD ID | ord-333e7770e9b3453c988cdb29fcb65840 |
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| Source note | uspto-grants-2001_06 |
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