Trifluoroacetic acid → HCID 21970616, compound

HRID 1067074Notes

Reaction equation

HRID 1067074 reaction equation
[CH2:1]([NH:8][C:9](=[O:56])[C@H:10]([CH2:35][CH2:36][CH2:37][NH:38]C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[N:11]([C:13](=[O:34])[C@H:14]([CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1)[NH:15]C(OC(C)(C)C)=O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCCC1.[F:63][C:64]([F:69])([F:68])[C:65]([OH:67])=[O:66]>CN(C)C=O>[F:63][C:64]([F:69])([F:68])[C:65]([OH:67])=[O:66].[CH2:1]([NH:8][C:9](=[O:56])[C@H:10]([CH2:35][CH2:36][CH2:37][NH2:38])[N:11]([C:13](=[O:34])[C@H:14]([CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1)[NH2:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 131722650HCID 131722650, compound

Product 1

HCID 21970616HCID 21970616, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-β-(1-Naphthyl)alanyl-Nδ-Fmoc-Nα-methylornithine benzylamide (B) (28 mg) was deprotected in teo steps-i) 20% piperidine in dimethylformamide and ii) trifluoroacetic acid exposure to afford a white solid: HPLC (method A); 1H NMR (400 MHz, D2O) δ1.59 (m, 2H), 1.77 (m, 1H), 1.89 (m, 1H), 2.38 (s, 3H), 3.0 (t, 2H), 3.60 (dd, 1H), 3.82 (dd, 1H), 4.39 (d, 2H), 4.92 (t, 1H), 5.01 (dd, 1H), 7.36-7.50 (m, 12H), 7.75 (m, 2H), 7.99 (t, 1H),8.10 (d, 1H), and 8.18 (d, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-f80e68966dae47d0a20bac4c311cead2
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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