Trifluoroacetic acid → HCID 86757007, compound

HRID 1067084Notes

Reaction equation

HRID 1067084 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:42])[C@H:13]([CH2:31][CH2:32][CH2:33][NH:34]C(OC(C)(C)C)=O)[N:14]([C:16](=[O:30])[C@H:17]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH:18]C(OC(C)(C)C)=O)[CH3:15].[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]>>[F:46][C:45]([F:48])([F:47])[C:43]([OH:49])=[O:44].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:42])[C@H:13]([CH2:31][CH2:32][CH2:33][NH2:34])[N:14]([C:16](=[O:30])[C@H:17]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:18])[CH3:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757008HCID 86757008, compound

Product 1

HCID 86757007HCID 86757007, compound

Procedure

N-Boc-leucyl-Nδ-Boc-Nα-methylornithine 2-naphthylamide was treated with TFA at 25° C. for 30 min. The solution was concentrated in vacuo and the residue purified by reverse phase HPLC (Amberchrome—CH3CN/0.1% TFA—H2O). The desired fraction was lyophilized to give titled product: 1H NMR (400 MHz, D2O) δ1.0-1.1 (m, 6H), 1.7-1.9 (m, 5H), 2.0-2.2 (m, 2H), 3.1-3.3 (m, 5H), 4.6-4.7 (m, 1H), 5.1-5.2 (m, 1H), 7.5-7.7 (m, 3H), and 7.9-8.1 (m, 4H); mass spectrum, m/e 384 (M+), 271, 241, 194, and 129.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue purified by reverse phase HPLC (Amberchrome—CH3CN/0.1% TFA—H2O)

Sources & evidence

ORD record
ord-bf0faf981d684c0685051d521ea6e9af
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

Loading…