Carbonazidic acid, 1,1-dimethylethyl ester → 2-(Benzyl(tert-butoxycarbonyl)amino)acetic acid

HRID 260459Notes

Reaction equation

HRID 260459 reaction equation
Cl.[CH2:2]([NH:9][CH2:10][C:11]([OH:13])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N+]=[N-].C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[C:17]([N:9]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:10][C:11]([OH:13])=[O:12])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 516892Sodium BicarbonateHCID 2756624N-Benzylglycine Hydrochloride

Product 1

HCID 105158162-(Benzyl(tert-butoxycarbonyl)amino)acetic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

N-Benzylglycine hydrochloride (7.38 g, 36.6 mmol), tert-butyl azidoformate (10.7 mL, 73.2 mmol) and sodium bicarbonate (12.3 g) were reacted in 150 mL dioxane/H2O-1:1 (v/v) at 45° (24 hr) and then at room temperature (24 h). The reaction suspension was evaporated to dryness and the resulting white residue was dissolved in 200 mL glacial acetic acid/H2O--1:1(v/v) with cooling to 4°. Water (800 ml) was slowly added with rapid stirring and cooling. The resulting turbid solution was seeded with Boc-N-benzyl-glycine obtained from Method A and allowed to stand in an ice bath for 30 min. The resulting material was gathered by filtration, washed with water followed by petroleum ether (bp 30°-75°) and dried to give 8.34 g (86%) of crude product as a white solid. Recrystallization from dichloromethane petroleum ether (bp 30°-75°) gave 7.34 g (76%) of white, crystalline product identical to Boc-N-benzylglycine (Method A) by NMR and melting point (106°).

Workup

  1. customat room temperature
  2. custom(24 h)
  3. customThe reaction suspension was evaporated to dryness
  4. dissolutionthe resulting white residue was dissolved in 200 mL glacial acetic acid/H2O--1:1(v/v)
  5. temperaturewith cooling to 4°
  6. additionWater (800 ml) was slowly added
  7. temperaturecooling
  8. filtrationThe resulting material was gathered by filtration
  9. washwashed with water
  10. customdried
  11. customto give 8.34 g (86%) of crude product as a white solid
  12. customRecrystallization from dichloromethane petroleum ether (bp 30°-75°)

Sources & evidence

ORD record
ord-437c5f159be84bb3a42ff57279936652
Source dataset
uspto-grants-1996_06
Patent number
US05527882

Reaction notes

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