Trifluoroacetic acid → HCID 178462175, compound

HRID 1067060Notes

Reaction equation

HRID 1067060 reaction equation
[CH3:1][C@@H:2]([NH:13]C(OC(C)(C)C)=O)[C:3](ON1C(=O)CCC1=O)=[O:4].[NH2:21][C@H:22]([C:30]([NH:32][C@H:33]([C:41]([OH:43])=O)[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.Cl.[CH:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][C:47]=1[NH-:56].[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60]>>[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60].[CH:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][C:47]=1[NH:56][C:41](=[O:43])[C@H:33]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])[NH:32][C:30](=[O:31])[C@H:22]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[NH:21][C:3](=[O:4])[C@@H:2]([CH3:1])[NH2:13]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11580086N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl esterHCID 178478816HCID 178478816, compound

Product 1

HCID 178462175HCID 178462175, compound

Procedure

This was similarly prepared, as described in Example 1. Boc-D-alanine N-hydroxysuccinimide ester was coupled to Phe-Arg-β-naphthylamide dihydrochloride; the resultant Boc-D-Ala-Phe-Arg 2-naphthylamide was deprotected with trifluoroacetic acid to afford a white solid: 1H NMR (400 MHz, D2O ) δ1.43 (d, J=8.8 Hz, 3H), 1.74 (m, 2H), 1.90 (m, 1H), 1.99 (m, 1H), 3.17 (dd, J=12.9; 8.2 Hz, 1H), 3.21 (dd, J=12.3; 8.2 Hz, 1H), 3.29 (t, J=7.1 Hz, 2H), 4.13 (q, J=8.8 Hz, 1H), 5.50 (t, J=8.0 Hz, 1H), 4.81 (HOD with proton hidden), 7.18 (m, 1H), 7.29 (m, 4H), 7.58 (d, J=10.6 Hz, 1H), 7.63 (m, 2H), and 8.01 (m, 4H).

Workup

  1. customThis was similarly prepared
  2. customto afford a white solid

Sources & evidence

ORD record
ord-63d3d347924742c69d945d78fb83277f
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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