Trifluoroacetic acid → HCID 22961303, compound

HRID 2304862Notes

Reaction equation

C([N:8]([C@@H:24]([C:33]1[O:34][CH:35]=[C:36]([C:38]([NH:40][C:41]2[CH:42]=[N:43][C:44]3[C:49]([CH:50]=2)=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:39])[N:37]=1)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9](=[O:23])[C@H:10]([NH2:22])[CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)(OC(C)(C)C)=O.[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54]>>[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54].[NH2:22][C@H:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:9]([NH:8][C@@H:24]([C:33]1[O:34][CH:35]=[C:36]([C:38]([NH:40][C:41]2[CH:42]=[N:43][C:44]3[C:49]([CH:50]=2)=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:39])[N:37]=1)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 70173258HCID 70173258, compound

Product 1

HCID 22961303HCID 22961303, compound

Procedure

2-[(1R)-1-[N,N′-Bis-Boc-(2R)-2,5-diaminovaleramido]-3-phenylpropyl]-N-(3-quinolyl)-4-oxazolecarboxamide (66 mg) was deprotected with trifluoroacetic acid to afford the title compound (68 mg) as a white powder: 1H NMR (400 MHz, D2O) δ 1.83 (m, 2H), 2.06 (m, 2H), 2.45 (m, 1H), 2.57 (m, 1H), 2.83 (m, 1H), 2.96 (m, 1H), 3.11 (t, J=8.3 Hz, 2H), 4.19 (t, J=6.0 Hz, 1H), 5.22 (t, J=7.4 Hz, 1H), 7.38 (m, 3H), 7.42 (m, 2H), 7.96 (t, J=9.0 Hz, 1H), 8.09 (t, J=9.0 Hz, 1H), 8.23 (m, 2H), 8.60 (s, 1H), 9.11 (s, 1H), and 9.48 (s, 1H).

Sources & evidence

ORD record: ord-0f46dcd82fea44b096ccc4d86a2a60f9
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436980B1

Reaction notes

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