Trifluoroacetic acid → HCID 86651891, compound

HRID 1183024Notes

Reaction equation

HRID 1183024 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:31][NH:32][C:33]([C:35]1[C:40]([NH2:41])=[N:39][C:38]([NH2:42])=[C:37]([Cl:43])[N:36]=1)=[O:34])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:30])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)(C)(C)C.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46]>C(Cl)Cl>[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[NH2:7][C@@H:8]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:30])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:21]=1)[CH2:31][NH:32][C:33]([C:35]1[C:40]([NH2:41])=[N:39][C:38]([NH2:42])=[C:37]([Cl:43])[N:36]=1)=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86651889HCID 86651889, compound

Product 1

HCID 86651891HCID 86651891, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ((S)-5-[2-(4-benzyloxy-phenyl)-acetylamino]-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (0.1 g, 0.16 mmol) in DCM (3 mL) and TFA (1 mL) is stirred at RT for 6 h. The solvent is removed in vacuo and the resulting residue is dissolved in DMSO and purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water-0.1% TFA) to afford the title compound. [M+H]+ 526. 1H NMR (500 MHz, DMSO-d6) δ 8.16 (1H, t), 8.05 (1H, t), 7.94 (4H, br), 7.42 (2H, d), 7.37 (2H, dd), 7.31 (1H, dd), 7.16 (2H, d), 7.04 (2H, br), 6.92 (2H, d), 5.05 (2H, s), 3.38 (2H, m), 3.31 (2H, s), 3.18 (1H, m), 3.02 (2H, m), 1.52 (2H, m), 1.38 (4H, m).

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe resulting residue is dissolved in DMSO
  3. custompurified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water-0.1% TFA)

Sources & evidence

ORD record
ord-c6abb862ef604597b4d39e20da4b8977
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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