Trifluoroacetic acid → Tyrosyl-Nalpha-Methylornithinyl 2-Naphthyl Ether Trifluoroacetate

HRID 1067106Notes

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[O:11][C:12](=[O:46])[C@H:13]([CH2:35][CH2:36][CH2:37][NH:38]C(OC(C)(C)C)=O)[N:14]([C:16](=[O:34])[C@H:17]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[NH:18]C(OC(C)(C)C)=O)[CH3:15].[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]>>[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12](=[O:46])[C@H:13]([CH2:35][CH2:36][CH2:37][NH2:38])[N:14]([C:16](=[O:34])[C@H:17]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=1)[NH2:18])[CH3:15]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 131722663Boc-Tyrosyl-Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl Ether

Product 1

HCID 131722664Tyrosyl-Nalpha-Methylornithinyl 2-Naphthyl Ether Trifluoroacetate

Procedure

Boc-Tyrosyl-Nδ-Boc-Nα-methylornithinyl 2-naphthyl ether (125 mg) was treated with trifluoroacetic acid (Procedure E) to afford titled product (100 mg) as a white solid: 1H NMR (400 MHz, D2O) δ1.77 (m, 4H), 2.78 (m, 3H), 3.08 (m, 4H), 4.06 (dd, J=11.4; 3.6 Hz, 1H), 4.17 (dd, J=1 1.5; 8.4 Hz, 1H), 4.72 (t, J=7.8 Hz, 1H), 4.89 (m, 1H), 6.65 (d, J=10.8 Hz, 2H), 7.17 (d, J=10.8 Hz, 2H), 7.22 (dd, J=9.6; 1.1 Hz, 1H), 7.34 (s, 1H), 7.51 (t, J=8.4 Hz, 1H), 7.61 (t, J=8.4 Hz, 1H), 7.94 (m, 3H).

Sources & evidence

ORD record: ord-f2a6893ca45040dd985133a7ca171395
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245746B1

Reaction notes

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