Trifluoroacetic acid → HCID 59627856, compound

HRID 1256663Notes

Reaction equation

HRID 1256663 reaction equation
C(OC([N:8]([C:16]1[C:21]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[CH:20][CH:19]=[C:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:17]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:26]([O:25][C:23](=[O:24])[NH:22][C:21]1[C:16]([NH2:8])=[N:17][C:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:19][CH:20]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59627868HCID 59627868, compound

Product 1

HCID 59627856HCID 59627856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of di-tert-butyl(3-{[(benzyloxy)carbonyl]amino}-6-phenylpyridin-2-yl)imidodicarbonate (359 mg, 0.691 mmol) and methylene chloride (2.76 mL) was treated with TFA (0.691 mL) in one portion. The reaction was stirred for 3 h, then concentrated via rotovap slowly to afford a residue purified via MPLC, silica cartridge, 0-5% MeOH in methylene chloride to afford the product as a light orange solid. 1H NMR (DMSO-d6, 600 MHz, rotamers present) δ 9.04 (br s, 1H), 7.86 (d, J=7.3 Hz, 1H), 7.47-7.30 (m, 5H), 7.15 (d, J=8.2 Hz, 1H), 6.40 (br s, 2H), 5.16 (s, 2H); MS cal'd 320 (M+H)+, exp 320 (M+H)+.

Workup

  1. concentrationconcentrated via rotovap slowly
  2. customto afford a residue
  3. custompurified via MPLC, silica cartridge, 0-5% MeOH in methylene chloride

Sources & evidence

ORD record
ord-aee56afd020f4a298798419d71d7d988
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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