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

HRID 1006119Notes

Reaction equation

HRID 1006119 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-7e6f706a6d28478c8ea2236c551bc829
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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