Trifluoroacetic acid → HCID 22851534, compound

HRID 1033684Notes

Reaction equation

HRID 1033684 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].COC1C=CC(C[S:23][C@@H:24]2[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[C@H:26]([C:42]([N:44]3[CH2:50][CH2:49][CH2:48][N:47]([CH2:51][CH2:52][O:53][C:54](=[O:56])[NH2:55])[CH2:46][CH2:45]3)=[O:43])[CH2:25]2)=CC=1>C1(OC)C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[C:54]([O:53][CH2:52][CH2:51][N:47]1[CH2:48][CH2:49][CH2:50][N:44]([C:42]([C@@H:26]2[CH2:25][C@H:24]([SH:23])[CH2:28][N:27]2[C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])=[O:43])[CH2:45][CH2:46]1)(=[O:56])[NH2:55]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 22851533HCID 22851533, compound

Product 1

HCID 22851534HCID 22851534, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

2.7 ml of trifluoroacetic acid and 88 μl of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 308 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-[4-(2-carbamoyloxyethyl) -1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine dissolved in 543 μl of anisole, and the resulting mixture was stirred a the same temperature for 1 hour. At the end of this time, the reaction mixture was worked up in a similar manner to that described in Example 32(1), to afford 315 mg of the title compound.

Sources & evidence

ORD record
ord-3979ccae2148485f9a48887af7eb2822
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

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