Trifluoroacetic acid → HCID 18342539, compound

HRID 2301188Notes

Reaction equation

HRID 2301188 reaction equation
[CH2:1]([N:8]1[N:12]=[N:11][C:10]([CH2:13][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C@@H:24]3[C@@H:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:27][N:26]([C@@H:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]4[CH2:41][C:42]([O:44]CC4C=CC(OC)=CC=4)=[O:43])[CH2:25]3)[CH2:19][CH2:18]2)[CH2:15][CH3:16])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:1]([N:8]1[N:12]=[N:11][C:10]([CH2:13][N:14]([CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][C@@H:24]3[C@@H:28]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:27][N:26]([C@@H:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]4[CH2:41][C:42]([OH:44])=[O:43])[CH2:25]3)[CH2:21][CH2:22]2)[CH2:15][CH3:16])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86758723HCID 86758723, compound

Product 1

HCID 18342539HCID 18342539, compoundYield 106.7%

Procedure

To 54 mg of 2-(R)-(3-(S)-((4-(N-(2-Benzyl-2H-tetrazol-5-yl)methyl-N-ethylamino)-piperidine-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-Methoxybenzyl ester (from Step E) were added 150 mg of anisole and 3 ml of triflouroacetic acid. The reaction was stirred at room temperature for 1 hour. The trifluoroacetic acid was evaporated under reduced pressure. The residue was purified by flash chromatography with 20% MeOH in EtOAc followed by 20% MeOH+2% NH4OH in EtOAc to give 48 mg of the title compound. ESI−MS 601 (M+H).

Workup

  1. customThe trifluoroacetic acid was evaporated under reduced pressure
  2. customThe residue was purified by flash chromatography with 20% MeOH in EtOAc

Sources & evidence

ORD record
ord-0d9f34f5a2d04fa29d1b6ce35ff80938
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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