Hydrochloric Acid → tert-butyl-2(R)-amino-3-phthalimido-propionate

HRID 2297999Notes

Reaction equation

HRID 2297999 reaction equation
[C:1]([O:5][C:6](=[O:28])[C@H:7]([NH:20]C(OC(C)(C)C)=O)[CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])([CH3:4])([CH3:3])[CH3:2].Cl.CC(C(OC)=O)=C>O1CCOCC1>[C:1]([O:5][C:6](=[O:28])[C@H:7]([NH2:20])[CH2:8][N:9]1[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]2[C:13]1=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6658Methyl MethacrylateHCID 18337585tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionate

Product 1

HCID 18337584tert-butyl-2(R)-amino-3-phthalimido-propionateYield 90.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimido-propionate (8.58 g, 21.8 mmol) was taken up in a anhydrous solution of hydrochloric acid in dioxane (100 ml, 4% wt/wt). The reaction flask was fitted with a rotovap trap, which was topped with a teflon stopper and the mixture was heated to 80° C. (use a plexiglass shield for safety). After 1.5 hours the material was cooled to ambient temperature and all volatiles removed on the rotary evaporator. The white solid was taken up in methylene chloride (100 ml) and transferred to a seperatory funnel. The solution was partitioned with an equal volume of aqueous sodium hydroxide (1.0 N) and the organic phase collected. This was subsequently shaken with brine solution (2×100 ml, consecutively) and the aqueous phases back extracted with methylene chloride (3×100 ml). The organic phases were combined, dried (MgSO4), filtered and condensed to provide tert-butyl-2(R)-amino-3-phthalimido-propionate (5.7 g) as a white powder.

Workup

  1. customThe reaction flask was fitted with a rotovap trap
  2. temperatureAfter 1.5 hours the material was cooled to ambient temperature
  3. customall volatiles removed on the rotary evaporator
  4. customtransferred to a seperatory funnel
  5. customThe solution was partitioned with an equal volume of aqueous sodium hydroxide (1.0 N)
  6. customthe organic phase collected
  7. extractionconsecutively) and the aqueous phases back extracted with methylene chloride (3×100 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customcondensed

Sources & evidence

ORD record
ord-20de131c4f2045b196bca83bb8b49847
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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