Trifluoroacetic acid → HCID 178485761, compound

HRID 1067063Notes

Reaction equation

HRID 1067063 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

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 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) δ1.70 (m, 2H), 1.92 (m, 1H), 2.15 (m, 1H), 2.82 (s, 3H), 3.42 (m, 4H), 4.83 (HOD with proton hidden), 5.19 (m, 1H), 7.18 (m, 2H), 7.31 (m, 1H), 7.68 (m, 4H), 8.15 (m, 4H), and 8.20 (s, 1H).

Workup

  1. customfollowed by HPLC purification (Method A)

Sources & evidence

ORD record
ord-bd6c2cf59ff641ac8931df06da04b8ed
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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