Trifluoroacetic acid → HCID 18654563, compound

HRID 2226025Notes

Reaction equation

HRID 2226025 reaction equation
[CH2:1]([N:6]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[N:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]([C:30]([N:32]([CH2:34][CH2:35][N:36](C)[C:37](OC(C)(C)C)=O)[CH3:33])=[O:31])[CH2:10]1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].C1(OC)C=CC=CC=1.[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61]>>[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61].[CH2:45]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:11]([C:30]([N:32]([CH2:34][CH2:35][NH:36][CH3:37])[CH3:33])=[O:31])[CH2:10]1)=[O:8])[CH2:46][CH2:47][CH2:48][CH3:49]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 19004119HCID 19004119, compound

Product 1

HCID 18654563HCID 18654563, compoundYield 98%

Procedure

To a mixture of 130 mg (0.19 mmole) of 4-(N,N-di-n-pentylcarbamoyl)-1-(N,N-diphenylcarbamoyl)-2-(2-(N-methyl-N-(t-butoxycarbonyl)amino)-N-(methyl)ethylaminocarbonyl)piperazine and 0.4 mL of anisole at 0° C. was added 2 mL of trifluoroacetic acid precooled to 0° C. After 45 min the solution was concentrated in vacuo and the residue purified by flash chromatography on 16 g of silica gel eluting with 100:9 CH2Cl2 :MeOH to give 130 mg (98%) of an oil.

Workup

  1. customprecooled to 0° C
  2. concentrationAfter 45 min the solution was concentrated in vacuo
  3. customthe residue purified by flash chromatography on 16 g of silica gel eluting with 100:9 CH2Cl2

Sources & evidence

ORD record
ord-2bb4e943ba154f4cb3a3c733975ece2c
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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