Trifluoroacetic acid → Benzoic anhydride

HRID 1598929Notes

Reaction equation

HRID 1598929 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[C:8]1([C:14](Cl)=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(N(CC)CC)C>[O:5]([C:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:15])[C:3]([C:2]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 7412Benzoyl chloride

Product 1

HCID 7167Benzoic anhydride

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

For the preparation of compounds of formula I, (Q1 is R1CO or PhCO), an intermediate VIII (Q1 is t-butoxycarbonyl) is treated with trifluoroacetic acid (TFA) as in the conversion of VII to VIII. The resulting TFA salt of the corresponding amino compound is then treated with an acid chloride of the formula R1COCl or PhCOCl or an anhydride of the formula (R1CO)2O or (PhCO)2O in the presence of a tertiary amine such as triethylamine to give VIII (Q1 is R1CO or PhCO). This is subsequently transformed into IX (Q1 is R1CO or PhCO) by the same procedure as for the conversion of VIII (Q1 is t-butoxycarbonyl or benzyloxycarbonyl) to IX (Q1 is t-butoxycarbonyl or benzyloxycarbonyl).

Sources & evidence

ORD record
ord-725616959f654987b1b3576f18dc24f8
Source dataset
uspto-grants-1998_04
Patent number
US05739279

Reaction notes

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