Trifluoroacetic acid → D-Ornithyl-D-phenylalaninyl 2-Naphthyl Thioether Trifluoroacetate

HRID 1067098Notes

Reaction equation

HRID 1067098 reaction equation
C(N[C@H](C(O)=O)CCCNC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[S:34][C:35](=[O:67])[C@@H:36]([CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[NH:37][C:38](=[O:59])[C@H:39]([CH2:48][CH2:49][CH2:50][NH:51]C(OC(C)(C)C)=O)[NH:40]C(OC(C)(C)C)=O.[F:68][C:69]([F:74])([F:73])[C:70]([OH:72])=[O:71]>>[F:68][C:69]([F:74])([F:73])[C:70]([OH:72])=[O:71].[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[S:34][C:35](=[O:67])[C@@H:36]([CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[NH:37][C:38](=[O:59])[C@@H:39]([CH2:48][CH2:49][CH2:50][NH2:51])[NH2:40]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7015803Boc-orn(boc)-OHHCID 20662195Nalpha,Ndelta-bis-Boc-ornithyl-D-phenylalaninyl 2-naphthyl thioether

Product 1

HCID 20662221D-Ornithyl-D-phenylalaninyl 2-Naphthyl Thioether Trifluoroacetate

Procedure

N-Boc-D-phenylalaninyl 2-naphthyl thioether was deprotected (Procedure E) to afford D-phenylalaninyl 2-naphthyl thioether trifluoroacetate which was coupled (Procedure B) with Nα,Nδ-bis-Boc-ornithine. The Nα,Nδ-bis-Boc-ornithyl-D-phenylalaninyl 2-naphthyl thioether was deprotected by exposure to trifluoroacetic acid to afford after HPLC purification the titled compound: 1H NMR (400 MHz, D2O) δ1.60-1.70 (4H), 2.64-2.70 (2H), 2.90-3.30 (3H), 3.41-3.50 (1H), 3.80-3.82 (1H), 4.39-4.41 (1H), 7.23-7.70 (8H), and 7.80-8.05 (4H); mass spectrum (relative intensity) m/e 408 (100, M+1).

Workup

  1. customto afford
  2. customafter HPLC purification the titled compound

Sources & evidence

ORD record
ord-00ff3dfbdc784374b292ba176824ad69
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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