Trifluoroacetic acid → HCID 178453263, compound

HRID 899164Notes

Reaction equation

HRID 899164 reaction equation
[C:1]([O:5][C:6](=[O:59])[NH:7][CH:8]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][C:52]=1[Cl:58])[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[CH2:13][CH:12]1[CH2:29][CH2:30][CH2:31][NH:32][C:33]([NH:42]C(OC(C)(C)C)=O)=[N:34]C(OC(C)(C)C)=O)=[O:10])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:59])[NH:7][CH:8]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][C:52]=1[Cl:58])[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[CH2:13][CH:12]1[CH2:29][CH2:30][CH2:31][NH:32][C:33]([NH2:42])=[NH:34])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454257HCID 178454257, compound

Product 1

HCID 178453263HCID 178453263, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, 20 mg (0.033 mmol) of the crude product 6-8 was reacted with 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (10 mg, 1.1 equivalents) and silver nitrate (6 mg, 1.1 eq) and NMM (2.2 equivalents) in 5 mL of acetonitrile at room temperature for 24 hours, followed by evaporation to remove the solvent and column chromatography purification to produce 4.5 mg of the product [2-[2-[3-(N′,N″-Di-tert-butoxycarbonyl-guanidino)-propyl]-4-(2-naphthalen-2-yl-ethyl)-piperazin-1-yl]-1-(2,4-dichloro-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (6-10). Product 6-10 (4.5 mg) was treated with 33% TFA in DCM at room temperature for 2 hours and the reaction mixture was concentrated and purified with HPLC to give 1.05 mg {1-(2,4-Dichloro-benzyl)-2-[2-(3-guanidino-propyl)-4-(2-naphthalen-2-yl-ethyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (6-11).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified with HPLC

Sources & evidence

ORD record
ord-cc773f49699046e389afc29d566c42fb
Source dataset
uspto-grants-2008_04
Patent number
US07354923B2

Reaction notes

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