Trifluoroacetic acid → HCID 178418937, compound

HRID 8527Notes

Reaction equation

HRID 8527 reaction equation
[C:1]([NH:4][CH:5]([CH2:60][C:61]1[CH:66]=[CH:65][C:64]([OH:67])=[CH:63][CH:62]=1)[C:6]([NH:8][CH:9]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=1)[C:10]([N:12]1[CH2:17][C:16](=[O:18])[N:15]([CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH2:14][CH:13]1[CH2:31][CH2:32][CH2:33][NH:34][C:35]([NH:44]C(OC(C)(C)C)=O)=[N:36]C(OC(C)(C)C)=O)=[O:11])=[O:7])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:4][CH:5]([CH2:60][C:61]1[CH:62]=[CH:63][C:64]([OH:67])=[CH:65][CH:66]=1)[C:6]([NH:8][CH:9]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=1)[C:10]([N:12]1[CH2:17][C:16](=[O:18])[N:15]([CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH2:14][CH:13]1[CH2:31][CH2:32][CH2:33][NH:34][C:35]([NH2:44])=[NH:36])=[O:11])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178418893HCID 178418893, compound

Product 1

HCID 178418937HCID 178418937, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-acetylamino-N-[2-[2-[3-(N′,N″-di-Boc-guanidino)propyl]-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)-propionamide, 36, (35 mg, 38 mmol), trifluoroacetic acid (1 mL) and dichloromethane (2 mL) is stirred at room temperature for 5 hours. The solution is concentrated in vacuo and the crude product purified over silica gel (acetonitrile:TFA:water) to afford 24 mg (86% yield) of the final product which corresponds to analog 227, Table IV.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. customthe crude product purified over silica gel (acetonitrile:TFA:water)

Sources & evidence

ORD record
ord-b3071ba7b71a49d8b139e5505012e8dc
Source dataset
uspto-grants-2006_08
Patent number
US07087759B2

Reaction notes

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