Boc-Phenylalanyl-Ndelta-Cbz-ornithinyl 2-Naphthyl Thioether → Phenylalanyl-Ornithinyl 2-Naphthyl Thioether Trifluoroacetate

HRID 1067092Notes

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[S:11][C:12](=[O:47])[C@H:13]([CH2:33][CH2:34][CH2:35][NH:36]C(OCC1C=CC=CC=1)=O)[NH:14][C:15](=[O:32])[C@H:16]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:17]C(OC(C)(C)C)=O.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].C([SiH](CC)CC)C>>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][C:12](=[O:47])[C@H:13]([CH2:33][CH2:34][CH2:35][NH2:36])[NH:14][C:15](=[O:32])[C@H:16]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH2:17]

Participants

Reactant 2

HCID 88211869Boc-Phenylalanyl-Ndelta-Cbz-ornithinyl 2-Naphthyl Thioether

HCID 131722655TFA triethylsilane

Product 1

HCID 20662292Phenylalanyl-Ornithinyl 2-Naphthyl Thioether Trifluoroacetate

Conditions

Temperature: 25 °C

Procedure

A solution of Boc-phenylalanyl-Nδ-Cbz-ornithinyl 2-naphthyl thioether (C) (30 mg) and a mixture of trifluoroacetic acid-triethylsilane (3:1) (10 ml) was stirred at 25° C. for 1 hr and concentrated in vacuo. The crude material was purified by HPLC to afford desired product (10 mg) as a white solid: HPLC (method A, retention time=46.26 min); 1H NMR (400 MHz, D2O) δ1.69 (m, 2H), 1.77 (m, 1H), 1.87 (m, 1H), 2.84 (t, J=8.4, 2H), 3.02 (m, 2H), 3.09 (dd, J=14.4; 7.2 Hz, 1H), 3.22 (dd, J=14.0 5.2 Hz, 1H), 4.15 (t, J=8.0 Hz, 1H), 7.16 (m, 2H), 7.34 (m, 3H), 7.48 (m, 1H), 7.60 (m, 3H), 7.93 (t, J=7.2, 1H), and 7.97 (m, 2H).

Workup

concentrationconcentrated in vacuo
customThe crude material was purified by HPLC

Sources & evidence

ORD record: ord-670add5f2def486398c2a106461955e8
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245746B1

Reaction notes

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