Trifluoroacetic anhydride → Pga1

HRID 46949

Reaction equation

HRID 46949 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 5280723Alprostadil

Product 1

HCID 5281912Pga1

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Alternately, the PGE1 -type compound is transformed to a bis-trifluoroacetate, for example by reaction with trifluoroacetic anhydride in the presence of pyridine in a solvent at 0° to 5° C., and thereafter contacted with a low-boiling alcohol (preferably b.p. below 110° C.) with a tertiary amine to form a PGA1 -type compound.

Sources & evidence

ORD record
ord-a11fac49e947493ab26228d4b32a677d
Source dataset
uspto-grants-1979_11
Patent number
US04175202

Linked notes

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