Trifluoroacetic acid → HCID 178485761, compound

HRID 1952731Notes

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[NH:11][C:12](=[O:55])[C@H:13]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[N:47]C(OC(C)(C)C)=O)[NH:39]C(OC(C)(C)C)=O)[N:14]([C:16](=[O:33])[C@H:17]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:18]C(OC(C)(C)C)=O)[CH3:15].[F:56][C:57]([F:62])([F:61])[C:58]([OH:60])=[O:59]>>[F:56][C:57]([F:62])([F:61])[C:58]([OH:60])=[O:59].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:55])[C@H:13]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:47])[N:14]([C:16](=[O:33])[C@H:17]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH2:18])[CH3:15]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178485757HCID 178485757, compound

Product 1

HCID 178485761HCID 178485761, compound

Procedure

Boc-Phenylalanyl-Nω,Nω'-bis-Boc-Nα-methylarginine β-naphthylamide was treated with trifluoroacetic acid (Procedure E), followed by HPLC purification (Method A) to afford a white solid (45 mg): 1H NMR (400 MHz, D2O) δ 1.70 (m, 2 H), 1.92 (m, 1 H), 2.15 (m, 1 H), 2.82 (s, 3H), 3.42 (m, 4 H), 4.83 (HOD with proton hidden), 5.19 (m, 1 H), 7.18 (m, 2 H), 7.31 (m, 1 H), 7.68 (m, 4 H), 8.15 (m, 4 H), and 8.20 (s, 1 H).

Workup

customfollowed by HPLC purification (Method A)

Sources & evidence

ORD record: ord-ce06cfabc7a9454b8b98134b9c1a35b4
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06114310

Reaction notes

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