4-Quinolinecarboxaldehyde → (r)-5-Methyl-1-quinol-4-ylmethyl-3-(4-trifluoromethanesulfonylphenyl)imidazolidine-2,4-dione trifluoroacetate

HRID 1169641Notes

Reaction equation

HRID 1169641 reaction equation
[NH:1]([C:8](OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:9])[C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH:35]=O)=[CH:27][CH:26]=1.[F:37][C:38]([F:50])([F:49])[S:39]([C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1)(=[O:41])=[O:40]>>[F:37][C:38]([F:50])([F:49])[C:5]([OH:7])=[O:6].[CH3:5][C@H:2]1[N:1]([CH2:35][C:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:25]=[CH:26][CH:27]=2)[C:8](=[O:9])[N:46]([C:45]2[CH:47]=[CH:48][C:42]([S:39]([C:38]([F:49])([F:37])[F:50])(=[O:40])=[O:41])=[CH:43][CH:44]=2)[C:3]1=[O:4]

Participants

4

Reactant 3

HCID 780724-QuinolinecarboxaldehydeHCID 1363154-Aminophenyl trifluoromethyl sulphoneHCID 688637(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxypropanoic acid

Product 1

HCID 10257574(r)-5-Methyl-1-quinol-4-ylmethyl-3-(4-trifluoromethanesulfonylphenyl)imidazolidine-2,4-dione trifluoroacetate

Procedure

The compound is prepared from 0.04 mmol of resin, 0.12 mmol of N-Fmoc-D-Ala(OH), 0.20 mmol of 4-quinolinecarboxaldehyde and 0.10 mmol of 4-(trifluoromethanesulfonyl)aniline, in the same way as in Example 1. After purification by preparative LC-MS, 10 mg of expected product are obtained.

Workup

  1. customAfter purification by preparative LC-MS, 10 mg of expected product
  2. customare obtained

Sources & evidence

ORD record
ord-791060b6bdce46dd85c14c076ddeae52
Source dataset
uspto-grants-2010_11
Patent number
US07825115B2

Reaction notes

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