(S)-4-(pyrrolidine-3-sulfonyl)-phenol trifluoroacetic acid → (2S,3S)-4-[1-(2-Fluoro-4-phenyl-butyl)-pyrrolidine-3-sulfonyl]-phenol

HRID 1280710Notes

Reaction equation

HRID 1280710 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:12][CH2:11][C@H:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:9]1.[F:23][CH:24]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:25]OS(C1C=CC(C)=CC=1)(=O)=O>>[F:23][C@@H:24]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:25][N:8]1[CH2:12][CH2:11][C@H:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:9]1

Participants

3

Reactant 2

HCID 69924492(S)-4-(pyrrolidine-3-sulfonyl)-phenol trifluoroacetic acidHCID 86584022(RS)-toluene-4-sulfonic acid 2-fluoro-4-phenyl-butyl ester

Product 1

HCID 10134204(2S,3S)-4-[1-(2-Fluoro-4-phenyl-butyl)-pyrrolidine-3-sulfonyl]-phenol

Procedure

The title compound, MS: m/e=378.3 (M+H+) was prepared from (S)-4-(pyrrolidine-3-sulfonyl)-phenol trifluoroacetic acid salt and (RS)-toluene-4-sulfonic acid 2-fluoro-4-phenyl-butyl ester.

Sources & evidence

ORD record
ord-2a6f2d7328dc430e9d40c457d982dc09
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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