Reaction #2275688

ord-3f67295fdaca46fca78f9eca296a8f09

Reaction equation

CC(=O)OCC(COC(C)=O)NC(=O)OC(C)(C)C
Acetic acid 3-acetoxy-2-tert-butoxycarbonylamino-propyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CC(=O)OCC([NH3+])COC(C)=O.O=C([O-])C(F)(F)F
product
CC(=O)OCC([NH3+])COC(C)=O.O=C([O-])C(F)(F)F
2-Acetoxy-1-acetoxymethyl-ethyl-ammonium trifluoroacetate

Reactants

CC(=O)OCC(COC(C)=O)NC(=O)OC(C)(C)C
Acetic acid 3-acetoxy-2-tert-butoxycarbonylamino-propyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherwhen the volatiles were removed at reduced pressure

Procedure

Acetic acid 3-acetoxy-2-tert-butoxycarbonylamino-propyl ester (7.2 g) was dissolved in trifluoroacetic acid (40 ml) and stirred at ambient temperature. Effervescence was rapid at the start and had stopped after 1 h when the volatiles were removed at reduced pressure to give the product as a viscous oil in quantitative yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08323619B2uspto-grants-2012_12